Relevant bibliographies by topics / C-glycosides

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Academic literature on the topic 'C-glycosides'

Author: Grafiati
Published: 4 June 2021
Last updated: 25 May 2024

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Journal articles on the topic "C-glycosides"

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Iguchi, Tomoki, Naoki Takahashi, and Yoshihiro Mimaki. "A Total of Eight Novel Steroidal Glycosides Based on Spirostan, Furostan, Pseudofurostan, and Cholestane from the Leaves of Cestrum newellii." Molecules 25, no. 19 (September 28, 2020): 4462. http://dx.doi.org/10.3390/molecules25194462.

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Previously, various steroidal glycosides were reported from plants of Cestrum species. However, phytochemical investigation has not been conducted on Cestrum newellii. A systematic phytochemical investigation of the leaves of C. newellii resulted in the isolation of eight novel steroidal glycosides (1–8), which were classified into three spirostanol glycosides (1–3), two furostanol glycosides (4 and 5), two pseudofurostanol glycosides (6 and 7), and one cholestane glycoside (8). In addition, three known cholestane glycosides (9–11) were isolated and identified. The structures of the new compounds were determined based on spectroscopic data and chemical transformations. Compounds 1 and 2 are spirostanol glycosides having hydroxy groups at C-2, C-3, C-12, and C-24 of the aglycone moiety. Although C. newellii is known to be a poisonous plant, the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide assay exhibited that none of the isolated compounds were cytotoxic to HL-60 human promyelocytic leukemia cells.
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Peng, Wenwen, Xiaoxiang Fu, Yuyan Li, Zhonghua Xiong, Xugen Shi, Fang Zhang, Guanghua Huo, and Baotong Li. "Phytochemical Study of Stem and Leaf of Clausena lansium." Molecules 24, no. 17 (August 28, 2019): 3124. http://dx.doi.org/10.3390/molecules24173124.

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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.
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Avilov, Sergey A., Olga A. Drozdova, Vladimir I. Kalinin, Anatoly I. Kalinovsky, Valentin A. Stonik, Elena N. Gudimova, Ricardo Riguera, and Carlos Jiménez. "Article." Canadian Journal of Chemistry 76, no. 2 (February 1, 1998): 137–41. http://dx.doi.org/10.1139/v97-218.

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Frondoside C (1) is a new sulfated nonholostane triterpene glycoside obtained (with the glycosides closed by aglycone structure as impurities) from the sea cucumber Cucumaria frondosa. Its structure has been elucidated on the basis of spectral data (NMR and MS) of compound 1 and of its desulfated derivative (2) obtained by solvolysis. Frondoside C (1) is just the seventh glycoside reported from sea cucumbers, having a lanostane-type aglycone devoid of the typical 18(20)- lactone ring.Key words: Cucumaria frondosa, sea cucumbers, frondosides, triterepene glycosides, antitumor activity.
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Wang, Xiaojing, and Paul H. Gross. "C-Glycoside Syntheses. 3. Diastereo-diversified C-Glycosides from D-Glucose." Journal of Organic Chemistry 60, no. 5 (March 1995): 1201–6. http://dx.doi.org/10.1021/jo00110a024.

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Wu, Tse Chong, Peter G. Goekjian, and Yoshito Kishi. "Preferred conformation of C-glycosides. 1. Conformational similarity of glycosides and corresponding C-glycosides." Journal of Organic Chemistry 52, no. 21 (October 1987): 4819–23. http://dx.doi.org/10.1021/jo00230a038.

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Goekjian, Peter G., Tse Chong Wu, and Yoshito Kishi. "Preferred conformation of C-glycosides. 6. Conformational similarity of glycosides and corresponding C-glycosides." Journal of Organic Chemistry 56, no. 22 (October 1991): 6412–22. http://dx.doi.org/10.1021/jo00022a038.

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Prakash, Indra, Sangphyo Hong, Gil Ma, Cynthia Bunders, Krishna P. Devkota, Romila D. Charan, Catherine Ramirez, and Tara M. Snyder. "Complete Structure Elucidation of New Steviol Glycosides Possessing 9 Glucose Units Isolated from Stevia rebaudiana." Natural Product Communications 12, no. 10 (October 2017): 1934578X1701201. http://dx.doi.org/10.1177/1934578x1701201008.

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In our continued effort to discover new diterpene glycoside sweeteners from Stevia rebaudiana Bertoni with a better taste profile than that of rebaudioside M, we have isolated three novel steviol glycosides with 9 glucose units, 3 at the C-13 site of the aglycone backbone and 6 at the C-19 site. Compounds 2-4 contain an additional tri-glucosyl unit attached to the C-19 glycoside region of rebaudioside M. For compounds 2 and 3 this unit is attached via the relatively rare 1→6 α-glycoside linkage. For compound 4 this additional unit is attached via the uncommon 1→3 α-glycoside linkage. In this paper, we describe the complete structure elucidation of novel diterpene glycosides with 9 sugar moieties by NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY, NOESY) and mass spectral data.
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Xie, Liangqin, Zeyuan Deng, Jie Zhang, Huanhuan Dong, Wei Wang, Banghuai Xing, and Xiaoru Liu. "Comparison of Flavonoid O-Glycoside, C-Glycoside and Their Aglycones on Antioxidant Capacity and Metabolism during In Vitro Digestion and In Vivo." Foods 11, no. 6 (March 20, 2022): 882. http://dx.doi.org/10.3390/foods11060882.

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Flavonoids are well known for their extensive health benefits. However, few studies compared the differences between flavonoid O-glycoside and C-glycoside. In this work, flavonoid O-glycoside (isoquercitrin), C-glycoside (orientin), and their aglycones (quercetin and luteolin) were chosen to compare their differences on antioxidant activities and metabolism during in vitro digestion and in vivo. In vitro digestion, the initial antioxidant activity of the two aglycones was very high; however, they both decreased more sharply than their glycosides in the intestinal phase. The glycosidic bond of flavonoid O-glycoside was broken in the gastric and intestinal stage, while the C-glycoside remained unchanged. In vivo, flavonoid O-glycoside in plasma was more elevated than C-glycoside on the antioxidant activity; however, flavonoid C-glycoside in urine was higher than O-glycoside. These results indicate that differences of flavonoid glycosides and their aglycones on antioxidant activity are closely related to their structural characteristics and metabolism in different samples. Aglycones possessed higher activity but unstable structures. On the contrary, the sugar substituents reduced the activity of flavonoids while improving their stability and helping to maintain antioxidant activities after digestion. Especially the C-glycoside was more stable because the stability of the C–C bond is higher than that of the C–O bond, which contributes to the difference between flavonoid O-glycoside and C-glycoside on the absorption and metabolism in vivo. This study provided a new perspective for comparing flavonoid O-glycoside, flavonoid C-glycoside, and their aglycones on their structure–activity relationship and metabolism.
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Soriano, I. R., R. E. Asenstorfer, O. Schmidt, and I. T. Riley. "Inducible Flavone in Oats (Avena sativa) Is a Novel Defense Against Plant-Parasitic Nematodes." Phytopathology® 94, no. 11 (November 2004): 1207–14. http://dx.doi.org/10.1094/phyto.2004.94.11.1207.

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The induction of defense compounds in oats (Avena sativa) in response to invasion by parasitic nematodes and to application of the wound hormone methyl jasmonate was examined. Oats cv. Quoll seedlings were challenged with Pratylenchus neglectus, Heterodera avenae, and Ditylenchus dipsaci and treated with 1 × 10-4 M methyl jasmonate. Three compounds, isolated in methanolic root and shoot extracts of oats, exhibiting an absorbance spectrum typical of flavone glycosides, were induced by nematode invasion and methyl jasmonate. These were identified as flavone-C-glycosides by mass spectrometry. The effect of the flavone-C-glycosides on the invasion by and development of cereal cyst nematode H. avenae was assessed using methanolic extracts of shoots and roots from methyl jasmonate-treated plants. Both extracts impaired nematode invasion and development. When the extracts were fractionated by high voltage paper electrophoresis, only one flavone-C-glycoside, O-methyl-apigenin-C-deoxyhexoside-O-hexoside, inhibited nematode invasion. The protective effect of the induction of flavone-C-glycosides in oats by methyl jasmonate was evaluated against H. avenae and P. neglectus. Treatment with methyl jasmonate reduced invasion of both nematodes and increased plant mass, compensating for damage caused by the nematodes, and is attributed to the active flavone-C-glycoside. The active compound, O-methyl-apigenin-C-deoxyhexoside-O-hexoside, has not been implicated previously in plant defense against any pest or pathogen, and appears to provide protection against the major cereal nematodes Heterodera and Pratylenchus.
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Zhang, Ruiqin, Ruiqi Tang, Jiahua Bi, Shanshan Shen, Qin Wu, Qihe Chen, and Yanjun Li. "Efficient Bioconversion of Stevioside and Rebaudioside A to Glucosylated Steviol Glycosides Using an Alkalihalobacillus oshimesis-Derived Cyclodextrin Glucanotransferase." Molecules 28, no. 3 (January 27, 2023): 1245. http://dx.doi.org/10.3390/molecules28031245.

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The enzymatic transglycosylation of steviol glycosides can improve the edulcorant quality of steviol glycosides. Cyclodextrin glucanotransferase (CGTase) is one of the most popular glucanotransferases applied in this reaction. Herein, the CGTase-producing strain Alkalihalobacillus oshimensis CGMCC 23164 was isolated from Stevia planting soil. Using mass spectrometry-based secretome profiling, a high-efficiency CGTase that converted steviol glycosides to glucosylated steviol glycosides was identified and termed CGTase-13. CGTase-13 demonstrated optimal transglycosylation activity with 10 g/L steviol glycoside and 50 g/L soluble starch as substrates at <40 °C. Under the above conditions, the conversion rate of stevioside and rebaudioside A, two main components of steviol glycosides, reached 86.1% and 90.8%, respectively. To the best of our knowledge, this is the highest conversion rate reported to date. Compared with Toruzyme® 3.0 L, the commonly used commercial enzyme blends, glucosylated steviol glycosides produced using CGTase-13 exhibited weaker astringency and unpleasant taste, faster sweetness onset, and stronger sweetness intensity. Thus, CGTase provides a novel option for producing high-quality glucosylated steviol glycoside products and has great potential for industrial applications.
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Dissertations / Theses on the topic "C-glycosides"

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JEGOU, ANNE. "Nouvelles syntheses de c-glycosides." Rennes 1, 1998. http://www.theses.fr/1998REN10128.

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Les c-glycosides sont des analogues de sucres dans lesquels un atome de carbone remplace l'atome d'oxygene anomerique. En tant qu'analogue, un c-glycoside, de surcroit stable a l'hydrolyse chimique ou enzymatique, peut interferer dans le metabolisme des glucides en inhibant les enzymes (glycosidases ou glycosyltransferases) qui sont necessaires a l'elaboration d'un glycoconjugue fonctionnel. Les acetals bicycliques 2:2:1 derivent du 6-o-pivaloyl-d-galactal via une reaction d'iodocyclisation. Leur ouverture regioselective par des c-nucleophiles nous a permis d'exploiter la geometrie particuliere de ces molecules pour synthetiser stereoselectivement des motifs c-furanosides. L'allyltrimethylsilane et le 2-(trimethylsilyloxy)furane ont ete en particulier utilises. La reactivite du 2-(trimethylsilyloxy)furane, ainsi que celle du 3-trimethylsilylmethyl-but-3-enoate de methyle, derive du dicetene, vis-a-vis de donneurs de glycopyranosyle, ont ete egalement etudiees. Ces deux nucleophiles permettent d'introduire, des l'etape de c-glycosylation, une chaine fonctionnalisee en position anomerique.
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Fleury, Adeline. "Synthèse de c-glycosides et daminoacides glycosyles trifluoromethyles." Thesis, Cergy-Pontoise, 2011. http://www.theses.fr/2011CERG0509/document.

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L’objectif de nos travaux consiste en la préparation de C-glycosides et d’aminoacides glycosylés trifluorométhylés dans le but d'obtenir des structures biologiquement actives stabilisées. L'intérêt des C-glycosides est lié à leur stabilité autorisant une pharmacocinétique plus appropriée pour un usage thérapeutique. La 1ière partie de mon travail a été de créer une liaison C-C en position anomérique d'un sucre par différentes méthodes d’alkylation, d’alcynylation à l’indium et par la réaction de Réformatsky. Ensuite après avoir fonctionnalisé les C-glycosides synthétisés, une étude tournée vers la synthèse d’aminoacides C-glycosylés par le biais d’alkylations énantiosélectives a été réalisée. Ensuite nous avons étudié la synthèse d’aminoacides glycosylés stabilisés par l’introduction d’un groupement trifluorométhylé en une position stratégique. D’abord nous avons étudié la synthèse d’aminoacides N-glycosylés obtenus par la réaction entre un aminoacide trifluorométhylé et un sucre. Le groupe fluoré, en  de l’azote, diminue la basicité de l’amine et empêche sa protonation. Ainsi, l’hydrolyse du lien anomérique est très défavorisée. Plusieurs conditions réactionnelles ont été étudiées. Le milieu acide protonique a montré des résultats encourageant notamment entre le 2-déoxy-glucose et un dipeptide trifluorométhylé. Ensuite nous avons travaillé sur la synthèse de O-glycosides. 2 stratégies ont été développé à partir d’un sucre trifluorométhylé. D’abord l’éthérification de Williamson a été étudié entre un sucre trifluorométhylé et différents dérivés halogénés. Cette voie a donné des résultats satisfaisant avec des dérivés halogénés linéaires uniquements. Puis la réaction de Mitsunobu a été étudié entre un sucre trifluorométhylé et différents alcools. La réaction donne des résultats variés dépendant de l’alcool. Cette voie nous a aussi permis de synthétiser des aminoacides O-glycosylés trifluorométhylé en utilisant la sérine comme alcool
The aim of our work consists in the preparation of C-glycosides and trifluorinated glycosylated aminoacids in order to obtain biogically active structures. The interest of such C-glycosides, is due to its stability. It allows a better pharmacokinetics to a therapeutic use. The first part of my work was to create a C-C bond at the anomeric position of a carbohydrate by different methods such as alkylation, alcynylation and Reformatsky reaction. Then, after functionalized these C-glycosides, a study on C-glycosylated aminoacids synthetized by an enantioselectiv alkylation way was made. The second part of my work was to synthesized stabilized glycoaminoacidsby the introduction of a trifluoromethylated group at a strategic position: at the anomeric position of the carbohydtare or at  position of the anomeric position of the carbohydtare. We first studied the synthesis of N-glycosides with a trifluoromethylated group at  position of the anomeric position of the carbohydtare. This strategy is based on the reaction of a protected sugar with a trifluoromethylated amine catalysed by an acid. Then we studied the synthesis of O-glycoaminoacids with a trifluoromethylated group at the anomeric position of the carbohydtare. Two strategies have been developed. The first one is the alkylation of Williamson. The second one is the reaction of Mitsunobu
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Levoirier, Eric. "Synthèse organique en phase aqueuse : nouvelle méthodologie d'accès aux C-glycosides, glycosides branchés et C-disaccharides." Paris 11, 2002. http://www.theses.fr/2002PA112284.

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L'intérêt porté aux C-glycosides ainsi qu'aux C-disaccharides s'est considérablement accentué depuis ces dernières années. Contrairement aux O-glicosides, ceux-ci sont en effet stables en milieu biologique car peu ou pas métabolisables. Ils présentent par affleurs souvent, des caractéristiques structurales similaires aux oligosaccharides naturels, gardant ainsi l'essentiel des propriétés biologiques. Toutefois, la préparation de ces dérivés est bien souvent longue et fastidieuse et nécessite notamment de nombreuses étapes successives de protection-déprotection. D'autre part, il a été récemment démontré l'intérêt synthétique de la réaction d'allylation de composés carbonyles dans les conditions de Barbier dans l'eau. Ce type de réactivité a donc été appliqué à la synthèse de C-glicosides et de C-disaccharides. Pour cela, la synthèse de deux dérivée glycosidiques présentant un motif halogénure allylique a été mise au point. Les dérivés 4-bromo-2-énopyranoside et 6-bromo-4-énopyranoside obtenus ont été utilisés pour l'allylation de différents aldéhydes en présence d'indium. Après fonctionnalisation de la double liaison, différents 2-C- et 4-C-hexoses ont ainsi sélectivement été obtenu. L'utilisation comme composé carbonylé d'un β-C-glycosylaldéhyde, a permis la préparation de β(1->2)- et β(1->4)-C-disaccharides avec des rendements satisfaisants. Enfin, un accès rapide à ce type d'aldéhydes a été trouvé. Cette stratégie utilise comme étape clé la préparation d'une β-C-glycosylcétone en une seule étape depuis l'hexose libre. Le β-C-glycosylaldéhyde est ensuite obtenu après trois étapes supplémentaires avec un bon rendement
The Synthesis of carbon-carbon linked disaccharides (C-disaccharides) is the subject of widespread current interest. Among the many methods developed for the synthesis of C-glycosides, C-branched sugars and C-disaccharides during the last 20 years, some have been efficient, although they still remain relatively complex, generally requiring many protection-deprotection steps. Recently, organic reactions in water have received much attention not only because water is an economical and environmentally friendly solvent but more especially because unique reactivities and selectivities are often exhibited in water. Among them, indium chemestry has captured much recent attention largely due to the discovery that indium can mediate the smooth coupling of allylic halide with aldehydes to give the corresponding homoallylic alcohols in aqueous media. After the synthesis of the key compounds, the 4-bromo-2-enopyranoside and the 6-bromo-4-enopyranoside, we report a very convenient protocol for the preparation of 2-C- and 4-C-branched sugars and β(1->2)- and β(1->4)-C-disaccharides under indium promoted Barbier-type allylation in aqueous media
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Bercich, Mark David. "Asymmetric syntheses of anthraquinonyl C-glycosides." Thesis, University of Auckland, 1997. http://hdl.handle.net/2292/2007.

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Syntheses of C2-anthraquinone aldehydes from the commercially available anthrarufin 11 have been investigated. A synthesis of the ketoaldehyde 5 in nine steps and 73% overall yield was achieved. Syntheses of 5 exploiting selective oxidations of either a C-bound allyl group via Wacker oxidation to introduce the methyl ketone functionality, or of a C-bound prop-l-enyl moiety via dihydroxylation and oxidative cleavage to generate the C2 formyl group were also developed. The aldehyde 81 was synthesised in seven steps and 81% overall yield from ll, and syntheses of the phenolic aldehydes 82, 95, and 96, the Cl benzyloxyaldehyde 104, and the anthracene aldehyde 107 have been developed. Hetero Diels-Alder reactions of several anthraquinone aldehydes with the dienes 6,120, and 121 using catalysis by the complex (+)-VO(hfc)2 115 were studied. Reactions of the aldehydes 5 and 81 proceeded readily using catalytic amounts of 115 and dichloromethane, chloroform, or toluene as solvent to give the adducts 128 or 131 indicating an endo selective pericyclic reaction pathway. The enantioselectivites of these reactions were typically 20-50%, with a best ee of 56% for a reaction between 81 and 6 catalysed by 0.2 equivalents of 115 at -78°C. Reactions of the 1-silyloxydienes 120 and 121 with aldehyde 8l catalysed by 115 to give the enone 130 also proceeded readily with a best ee of 64% being obtained for a reaction between 81 and l2l in toluene at -78°C. Reactions of the phenolic aldehydes 95 and 96 and the diene 6, catalysed by 115, afforded good yields of cycloadducts, but with enantioselectivities identical to equivalent reactions of the aldehyde 81. However reactions of the Cl benzyloxyaldehyde 104 with the dienes 6 and 120, and 121 afforded cycloadducts with enantioselectivities lower than those from the equivalent reactions of the aldehyde 81. Elaboration of the cycloadduct 131 to the anthracene C-glycoside 149 established that the hetero Diels-Alder reaction had favoured the formation of the 2'R, 6'R enantiomer of 131. This enantiofacial selectivity was correlated with the sense of anisochrony observed in 1H NMR spectra of the ketone 129, derived from 131, in the presence of the chiral solvating agent (S)(+)-trifluoroanthrylethanol. The enone 130 was elaborated to the anthraquinone-olivose C-glycoside 154 demonstrating the utility of hetero Diels-Alder reactions involving silyloxydienes with Cl silyloxy and Cl methyl substituents for such syntheses. Attempts to use chiral acyloxyborane comploxes such as 168 and 169 as catalysts for hetero Diels-Alder reactions of the aldehydes 5, 81 and 107 with the dienes 6 and 120 were unsuccessful. However two equivalents of the chiral acyloxyborane complex 168a in dichloromethane at 30°C, mediated. a formal hetero Diels-Alder reaction between 81 and 120 affording the enone 13O in 45% yield, with a 79% ee in favour of the 6'R enantiomer. Reactions catalysed by the chiral acyloxyborane complex 169b between beenzaldehyde or o-anisaldehyde and the dienes 6,119, and 120 gave products resulting from a Mukaiyama aldol addition rather than a hetero Diels-Alder reaction. Hetero Diels-Alder reactions 81 and 120 employing the chiral titanium complexes Ti[(R)-BINOL]C12, Ti[(R)-BINOL]2, and Ti[R,R)-TADDOL]C12 were investigated. No reaction was observed when 0.5, 1.2 and 2 equivalents of Ti[(R)-BINOL]2 were used. However the complexes Ti[(R)-BINOL]C12 and Ti[(R,R)-TADDOL]C12 promoted the reaction between 81 and 120 at -30°C and -78°C, but induced low enantioselectivities (17-30%)
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Gremyachinskiy, Dmitriy Y. "Total Synthesis of Aminomethyl C-glycosides." Scholarly Commons, 2000. https://scholarlycommons.pacific.edu/uop_etds/3765.

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Prince-type cyclizations were performed with different Lewis acids to select optimal conditions, for the synthesis of a series of 4-chloro-2- phtalimidomethyl 6-methyl tetrahydropyrans and 4-chIoro-2.6- bis(phtalimido-methyl)-tetrahvdropyrans. The total yield for phtalimidomethyl products reached 92%, and for bis-phtalimido compounds 71%. An influence of reagent size and nucleophilicitv on the reaction outcome was observed, and was interpreted in terms of cationic mechanism and complex formation in the transition state. A cyclization step was also used to synthesize bicvclic compounds that can be used as precursors for the synthesis of C-oligosaccandes. Optimized eliminations of hydrogen halide by DBU in presence of LiCl yielded a mixture of 2.6-anhydro-1.3.4.5.7- penradeoxy-l-phtahmido-DA-erythrohepr-3-emto! 5b and 2.6-anhydrol, 3,4,5,7-pentadeoxy-l-phtalimido-D.L-erythrohept-4-enitoI 6b in 79°a yield for the isomeric mixture. Epoxidation of this alkene mixture by a newly developed method with urea-hydrogen peroxide complex and trifluoroaceric anhydride afforded a mixture of epoxy-2-methvl-6- phtalimidomethyl tetrahydropyrans in 92% total yield. Epoxides were cleaved by aq. CF3COOH to give a mixture of dihydroxy-2-methyi-6- phtalimi dome by 1 tetrahydropyrans with an overall yield of 74% from the mixture of 5b/6b. The regioisomers were separated and deprotected by a newly developed method, and were oxidized to produce partially functionalized racemic aminomethyl C-glycopyranosides. One of the isomers was characterized as an N-acetyl-di-O-acetyl derivative and as a NBoc di-O-acetyl derivative, because this isomer was very hygroscopic. It was also found that transallylation occurred between acetal and homoallylic alcohol during the cyclization step. A new method for the synthesis of homoallylic alcohols from acetals was developed on the basis of this observation. Homoallylic alcohols, l-Benzyloxv-4-penten-2-ol 19. 1- Phenyl-4-pentene-2-ol 18 and BPhtalimido-4-pentene-2-ol 1β were synthesized by a new method with yields of 40%. 61 % and / i % respectively. The as yet unoptimized method allows to synthesize homoallylic alcohols from unstable aldehydes.
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Gremyachinskiy, Dmitriy. "Total synthesis of aminomethyl c-glycosides." Scholarly Commons, 2000. https://scholarlycommons.pacific.edu/uop_etds/544.

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REKAI, EL DJOUHAR. "Synthese selective de c-glycosides par cyclisation radicalaire : preparation de c-glycosides cycliques complexes, de c-disaccharides et de trisaccharides mixtes." Paris 6, 1997. http://www.theses.fr/1997PA066525.

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Le travail effectue au cours de la these s'inscrit dans le cadre des activites de recherche du laboratoire du professeur pierre sinay. Il porte sur l'etablissement de nouvelles methodes de synthese de c-glycosides. Nos recherches, se sont en premier lieu, tournees vers la synthese de c-glycosides cycliques tres particuliers, obtenus par cyclisation radicalaire a l'aide de l'iodure de samarium ii. Au cours de cette recherche, des resultats inattendus lors de reactions de cyclisation radicalaires sur des cycles aromatiques, ainsi que des reactions de cyclisation de type 5-exo-trig, se sont reveles tres interessants. Il est en fait envisageable que cette generation de nouveaux c-glycosides cycliques complexes, donnent acces apres quelques modifications chimiques a de longues chaines carbonees hautement fonctionnalisees, pouvant etre incorporees notamment a la synthese de macrolides. Nous nous sommes egalement interesses a la synthese de c-disaccharides contenant du l-fucose et du d-galactose par emploi de deux types d'agrafes : - agrafe au silicium, - agrafe paramethoxybenzylacetalique. Apres comparaison des methodes, il semble que ces deux types d'agrafages se valent l'un l'autre. De plus, nous avons montre que la stereochimie des c-disaccharides contenant du l-fucose et du d-galactose, est fonction non seulement de la nature des sucres (galactose ou fucose), mais egalement de la nature des groupements protecteurs, du type d'agrafage employe et de la position d'agrafage utilisee. Des regles simples de cyclisation concernant le l-fucose et le d-galactose ont pu etre etablies. Dans un troisieme temps, nous avons applique ces regles a la synthese de l'analogue carbone du determinant antigenique h du groupe sanguin humain o. Cet analogue carbone a ete modifie puis teste dans des reactions de o-glycosylation afin d'analyser sa reactivite chimique et former des trisaccharides mixtes.
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James, M. R. "Synthetic studies towards C-glycosides and spiroacetals." Thesis, University of Newcastle Upon Tyne, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.356787.

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Chaguir, Brahim. "C-glycosides insaturés : synthèse et étude structurale." Lyon 1, 1992. http://www.theses.fr/1992LYO10266.

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Les composes a methylene active reagissent sur le 4,6-di-o-benzyl-2,3-dideoxy-d- erythro hex-2-enopyranoside et , en presence de quantite catalytique de palladium (0), pour donner les c-glycosides correspondants. Cette methodologie de formation de la liaison c-c est hautement stereoselective conduisant a des molecules fonctionnalisables soit sur la partie sucre, soit sur le substituant glycosidique. Si le seul anomere est obtenu a partir du phenylglycoside le phenylglycoside conduit, selon la nature du nucleophile, au seul anomere ou a un melange d'anomeres /. La raison de la perte de selectivite est due a l'intervention du proton restant dans le compose d'alkylation, via une reaction de type retro-michael. Pour mettre au point les modifications structurales ulterieures des c-glycosides, nous avons synthetise le 2-phenoxy (2h)-5-6-dihydropyrane comme substrat modele en grande quantite et nous avons montre que la reaction de couplage a l'aide d'un complexe de palladium (0) s'effectuait egalement sur ce phenylglycoside simple. Les bases puriques et pyrimidiques reagissent sur le phenylglycoside , en presence de palladium (0), pour conduire de facon tres stereoselective a des n-glycopyranosides insatures. L'etude comparative par diverses techniques spectrales des isomeres et montre que: 1) la rmn est une methode de choix pour l'attribution de la configuration au niveau du carbone anomere (constante de couplage j#4##,#5#, c-5, effet noe). Cependant la methode de choix est l'effet noe, surtout si on est en presence d'un seul anomere, 2) en spectrometrie de masse, la technique fab associee a la technique (ms/ms) mike et cad-mike en ionisation chimique ou en presence de metaux alcalins (li#+, k#+, na#+ et rb#+) permet de definir pour chaque anomere une empreinte digitale specifique, 3) en dichroisme circulaire, les anomeres presentent un effet cotton positif et les anomeres un effet cotton negatif
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Paterson, Duncan Ewan. "A Ramberg-Bäcklund approach to C-glycosides and C-linked disaccharides." Thesis, University of York, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.323687.

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Books on the topic "C-glycosides"

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Levy, D. E. The chemistry of C-glycosides. Oxford, OX, U.K: Pergamon, 1995.

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Postema, Maarten H. D. C-Glycoside synthesis. Boca Raton, Fla: CRC Press, 1995.

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Hoffmann, Michael G. O-Glycosylimidate zur Synthese von funktionell substituierten Alkyl-C-glycosiden. Konstanz: Hartung-Gorre, 1985.

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Frick, Wendelin. C-C-Kettenverlängerung mit Zuckeraldehyden: Synthese von Papulacandin, Vitexin, Bergenin und KDO. Konstanz: Hartung-Gorre, 1991.

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Levy, D. E., and C. Tang. Chemistry of C-Glycosides. Elsevier Science & Technology Books, 1995.

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Levy, D. E., and C. Tang. Chemistry of C-Glycosides. Elsevier Science & Technology Books, 1995.

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The Chemistry of C-Glycosides. Elsevier, 1995. http://dx.doi.org/10.1016/s1460-1567(06)x8001-7.

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Postema, Maarten H. D. C-Glycoside Synthesis. Taylor & Francis Group, 2019.

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Kahl, Jennifer Lynn. A method for Ý-thioethylation of hydroxyl groups and stereoselective synthesis of C-glycosides. 1994.

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Postema, Maarten. C-Glycoside Synthesis. Taylor & Francis Group, 2020.

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Book chapters on the topic "C-glycosides"

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Brito-Arias, Marco. "C-Glycosides." In Synthesis and Characterization of Glycosides, 367–402. Cham: Springer International Publishing, 2022. http://dx.doi.org/10.1007/978-3-030-97854-9_5.

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Brito-Arias, Marco. "C-glycosides." In Synthesis and Characterization of Glycosides, 281–309. Cham: Springer International Publishing, 2016. http://dx.doi.org/10.1007/978-3-319-32310-7_5.

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Bucar, F., J. B. Xiao, and S. Ochensberger. "Flavonoid C-Glycosides in Diets." In Handbook of Dietary Phytochemicals, 1–37. Singapore: Springer Singapore, 2020. http://dx.doi.org/10.1007/978-981-13-1745-3_6-1.

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Bucar, F., Jianbo Xiao, and S. Ochensberger. "Flavonoid C-Glycosides in Diets." In Handbook of Dietary Phytochemicals, 117–53. Singapore: Springer Singapore, 2021. http://dx.doi.org/10.1007/978-981-15-4148-3_6.

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Goekjian, Peter G., Alexander Wei, and Yoshito Kishi. "Conformational Analysis of C-Glycosides and Related Compounds: Programming Conformational Profiles of C- and O-Glycosides." In Carbohydrate-Based Drug Discovery, 305–40. Weinheim, FRG: Wiley-VCH Verlag GmbH & Co. KGaA, 2005. http://dx.doi.org/10.1002/3527602437.ch11.

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Nicotra, Francesco. "Synthesis of C-glycosides of biological interest." In Glycoscience Synthesis of Substrate Analogs and Mimetics, 55–83. Berlin, Heidelberg: Springer Berlin Heidelberg, 1997. http://dx.doi.org/10.1007/bfb0119253.

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Yamamoto, Yoshihiko. "Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors." In Topics in Heterocyclic Chemistry, 215–60. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2018_27.

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Giurleo, Daniel J., H. Rodolfo Juliani, Larry S. Amekuse, Julie Asante Dartey, James E. Simon, and Qingli Wu. "Flavone C-Glycosides and Total Antioxidant Capacities in Leaves of Eight Wild Griffonia simplicifolia Populations." In ACS Symposium Series, 249–64. Washington, DC: American Chemical Society, 2020. http://dx.doi.org/10.1021/bk-2020-1361.ch012.

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Snook, Maurice E., Neil W. Widstrom, Billy R. Wiseman, Richard C. Gueldner, Richard L. Wilson, David S. Himmelsbach, John S. Harwood, and Catherine E. Costello. "New Flavone C-Glycosides from Corn (Zea maysL.) for the Control of the Corn Earworm (Helicoverpa zea)." In ACS Symposium Series, 122–35. Washington, DC: American Chemical Society, 1994. http://dx.doi.org/10.1021/bk-1994-0557.ch010.

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Lemaire, Sébastien, and Didier Schils. "Development of Efficient Routes to Access C-Glycosides as SGLT-2 Inhibitors for the Treatment of Type 2 Diabetes." In Topics in Heterocyclic Chemistry, 29–50. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/7081_2015_166.

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Conference papers on the topic "C-glycosides"

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Freitas, Juliano C. R., Wagner C. C. dos Santos, Bruna L. da Silva, Paulo H. Menezes, and Roberta A. Oliveira. "Stereoselective Synthesis of C-Glycosides using Potassium Aryltrifluoroborates." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0220-1.

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Riemann, Ingo, and Wolf-Dieter Fessner. "C-GLYCOSIDES FROM UNPROTECTED SUGARS (1) MECHANISTIC STUDIES." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.632.

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Riemann, Ingo, and Wolf-Dieter Fessner. "C-GLYCOSIDES FROM UNPROTECTED SUGARS (2) SCOPE OF PREPARATIVE APPLICATIONS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.462.

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Griffin, Frank K., Duncan E. Paterson, and Richard J. K. Taylor. "A NEW ROUTE TO EXO-GLYCALS, C-GLYCOSIDES AND C-LINKED DISACCHARIDES USING THE RAMBERG-BACKLUND REARRANGEMENT." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.585.

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Sprenger, Friedrich K. (Fitz), Frederik Diness, Inge Lundt, and Arnold E. Stutz. "C-GLYCOSIDES OF 4-AMINO-4-DEOXY-D-ARABINOFURANOSE: PRECURSORS EN ROUTE TO GLYCOSIDASE INHIBITING BROUSSONETINES." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.638.

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Chiara, Jose Luis, and Esther Sesmilo. "INTERMOLECULAR REDUCTIVE CROSS-COUPLING OF EPOXIDES AND CARBONYL COMPOUNDS: A NEW AVENUE FOR THE EFFICIENT AND STEROCONTROLLED PREPARATION OF C-GLYCOSIDES FROM 1,2-ANHYDROSUGARS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.579.

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Al-Samarrai, Othman Rashid, Nazar Ahmed Naji, and Rafah Razooq Hameed Al-Samarrai. "Effect of Myrrh and its isolated flavonoids and glycosides on the levels of pancreatic β-Cells hormones (preptin, insulin and C-peptide) in local Iraqi female rabbits." In 1ST SAMARRA INTERNATIONAL CONFERENCE FOR PURE AND APPLIED SCIENCES (SICPS2021): SICPS2021. AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0121143.

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Gervay-Hague, Jacquelyn, Janos Csanadi, and Jessica Wong. "C-GLYCOSIDE SULFONES AS POTENTIAL INHIBITORS OF SCLC METASTASES." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.458.

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Borodkin, Vladimir S., and Andrei V. Nikolaev. "SYNTHESIS OF C-GLYCOSIDE (PHOSPHONO) ANALOGUES OF LEISHMANIA PHOSPHOGLYCAN FRAGMENTS." In XXIst International Carbohydrate Symposium 2002. TheScientificWorld Ltd, 2002. http://dx.doi.org/10.1100/tsw.2002.461.

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Reports on the topic "C-glycosides"

1

Borch, Thomas, Yitzhak Hadar, and Tamara Polubesova. Environmental fate of antiepileptic drugs and their metabolites: Biodegradation, complexation, and photodegradation. United States Department of Agriculture, January 2012. http://dx.doi.org/10.32747/2012.7597927.bard.

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Many pharmaceutical compounds are active at very low doses, and a portion of them regularly enters municipal sewage systems and wastewater-treatment plants following use, where they often do not fully degrade. Two such compounds, CBZ and LTG, have been detected in wastewater effluents, surface waters, drinking water, and irrigation water, where they pose a risk to the environment and the food supply. These compounds are expected to interact with organic matter in the environment, but little is known about the effect of such interactions on their environmental fate and transport. The original objectives of our research, as defined in the approved proposal, were to: Determine the rates, mechanisms and products of photodegradation of LTG, CBZ and selected metabolites in waters exposed to near UV light, and the influence of DOM type and binding processes on photodegradation. Determine the potential and pathways for biodegradation of LTG, CBZ and selected metabolites using a white rot fungus (Pleurotusostreatus) and ADP, and reveal the effect of DOM complexation on these processes. Reveal the major mechanisms of binding of LTG, CBZ and selected metabolites to DOM and soil in the presence of DOM, and evaluate the effect of this binding on their photodegradation and/or biodegradation. We determined that LTG undergoes relatively slow photodegradation when exposed to UV light, and that pH affects each of LTG’s ability to absorb UV light, the efficiency of the resulting reaction, and the identities of LTG’sphotoproducts (t½ = 230 to 500 h during summer at latitude 40 °N). We observed that LTG’sphotodegradation is enhanced in the presence of DOM, and hypothesized that LTG undergoes direct reactions with DOM components through nucleophilic substitution reactions. In combination, these data suggest that LTG’s fate and transport in surface waters are controlled by environmental conditions that vary with time and location, potentially affecting the environment and irrigation waters. We determined that P. ostreatusgrows faster in a rich liquid medium (glucose peptone) than on a natural lignocellulosic substrate (cotton stalks) under SSF conditions, but that the overall CBZ removal rate was similar in both media. Different and more varied transformation products formed in the solid state culture, and we hypothesized that CBZ degradation would proceed further when P. ostreatusand the ᵉⁿᶻʸᵐᵃᵗⁱᶜ ᵖʳᵒᶠⁱˡᵉ ʷᵉʳᵉ ᵗᵘⁿᵉᵈ ᵗᵒ ˡⁱᵍⁿⁱⁿ ᵈᵉᵍʳᵃᵈᵃᵗⁱᵒⁿ. ᵂᵉ ᵒᵇˢᵉʳᵛᵉᵈ ¹⁴C⁻Cᴼ2 ʳᵉˡᵉᵃˢᵉ ʷʰᵉⁿ ¹⁴C⁻ᶜᵃʳᵇᵒⁿʸˡ⁻ labeled CBZ was used as the substrate in the solid state culture (17.4% of the initial radioactivity after 63 days of incubation), but could not conclude that mineralization had occurred. In comparison, we determined that LTG does not degrade in agricultural soils irrigated with treated wastewater, but that P. ostreatusremoves up to 70% of LTG in a glucose peptone medium. We detected various metabolites, including N-oxides and glycosides, but are still working to determine the degradation pathway. In combination, these data suggest that P. ostreatuscould be an innovative and effective tool for CBZ and LTG remediation in the environment and in wastewater used for irrigation. In batch experiments, we determined that the sorption of LTG, CBZ and selected metabolites to agricultural soils was governed mainly by SOM levels. In lysimeter experiments, we also observed LTG and CBZ accumulation in top soil layers enriched with organic matter. However, we detected CBZ and one of its metabolites in rain-fed wheat previously irrigated with treated wastewater, suggesting that their sorption was reversible, and indicating the potential for plant uptake and leaching. Finally, we used macroscale analyses (including adsorption/desorption trials and resin-based separations) with molecular- level characterization by FT-ICR MS to demonstrate the adsorptive fractionation of DOM from composted biosolids by mineral soil. This suggests that changes in soil and organic matter types will influence the extent of LTG and CBZ sorption to agricultural soils, as well as the potential for plant uptake and leaching.
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