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Journal articles on the topic 'Osmylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Brovetto, Margarita, Valeria Schapiro, Gabriel Cavalli, Paula Padilla, Ana Sierra, Gustavo Seoane, Leopoldo Suescun, and Raul Mariezcurrena. "Osmylation of chiral cis-cyclohexadienediols." New Journal of Chemistry 23, no. 5 (1999): 549–55. http://dx.doi.org/10.1039/a900732f.

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2

Tsui, Hon-Chung, and Leo A. Paquette. "Olefin Cleavage under Osmylation Conditions." Journal of Organic Chemistry 63, no. 22 (October 1998): 8071–73. http://dx.doi.org/10.1021/jo9812983.

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3

Al-Fouti, Khaled, and James R. Hanson. "The Stereochemistry of Osmylation of 2- and 17-Methylene-5α-Androstanes." Journal of Chemical Research 2003, no. 4 (April 2003): 232–33. http://dx.doi.org/10.3184/030823403103173606.

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Osmylation of 2-methylene-5α-androstan-17-one has been shown to afford the 2α-hydroxy-2β-hydroxymethyl derivative whilst 3β-hydroxy-17-methylene-5α-androstane gives the 17α-hydroxy-17β-hydroxymethyl derivative; the facial selectivity of these reactions is discussed.

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4

BAUM, RUDY. "C enantiomers resolved by osmylation technique." Chemical & Engineering News 71, no. 26 (June 28, 1993): 35–36. http://dx.doi.org/10.1021/cen-v071n026.p035.

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5

Gurjar, M. K., and Anupama S Mainkar. "Catalytic osmylation of allyl D-glucopyranoside." Tetrahedron: Asymmetry 3, no. 1 (January 1992): 21–24. http://dx.doi.org/10.1016/s0957-4166(00)82306-x.

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6

Jarosz, Sławomir. "Osmylation of higher sugar allylic alcohols." Carbohydrate Research 183, no. 2 (December 1988): 209–15. http://dx.doi.org/10.1016/0008-6215(88)84075-8.

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7

Poli, Giovanni. "The osmylation of flexible 3-substituted cyclopentenes." Tetrahedron Letters 30, no. 52 (January 1989): 7385–88. http://dx.doi.org/10.1016/s0040-4039(00)70704-0.

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8

Annunziata, Rita, Mauro Cinquini, Franco Cozzi, and Laura Raimondi. "Stereoselective osmylation of 5-vinyl-4,5-dihydroisoxazoles." Journal of the Chemical Society, Chemical Communications, no. 7 (1985): 403. http://dx.doi.org/10.1039/c39850000403.

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9

Cui, Marko Burghard, and Klaus Kern. "Reversible Sidewall Osmylation of Individual Carbon Nanotubes." Nano Letters 3, no. 5 (May 2003): 613–15. http://dx.doi.org/10.1021/nl034135p.

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10

Français, Antoine, Olivier Bedel, and Arnaud Haudrechy. "Is osmylation always preferring the richest double bond?" Tetrahedron 64, no. 11 (March 2008): 2495–524. http://dx.doi.org/10.1016/j.tet.2007.11.068.

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11

Hawkins, Joel M., Timothy A. Lewis, Stefan D. Loren, Axel Meyer, James R. Heath, Yoko Shibato, and Richard J. Saykally. "Organic chemistry of C60 (buckminsterfullerene): chromatography and osmylation." Journal of Organic Chemistry 55, no. 26 (December 1990): 6250–52. http://dx.doi.org/10.1021/jo00313a009.

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12

GURJAR, M. K., and A. S. MAINKAR. "ChemInform Abstract: Catalytic Osmylation of Allyl D-Glucopyranoside." ChemInform 23, no. 17 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199217267.

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13

Bernardi, Anna, Silvia Cardani, Carlo Scolastico, and Roberto Villa. "Catalytic osmylation of electron poor allylic alcohols and ethers." Tetrahedron 44, no. 2 (January 1988): 491–502. http://dx.doi.org/10.1016/s0040-4020(01)85840-3.

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14

Fleming, Ian, Achintya K. Sarkar, and Andrew P. Thomas. "The stereochemistry of osmylation, epoxidation, and methylenation of allylsilanes." Journal of the Chemical Society, Chemical Communications, no. 3 (1987): 157. http://dx.doi.org/10.1039/c39870000157.

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15

Černý, Václav. "An alternative route to 2α,3α-diols from 2,3-unsaturated 5α-steroids avoiding the use of osmium tetroxide." Collection of Czechoslovak Chemical Communications 54, no. 8 (1989): 2211–17. http://dx.doi.org/10.1135/cccc19892211.

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A method for preparation of 2α,3α-dihydroxy-5α-steroids from 2,3-unsaturated 5α-steroids without the use of OsO4 is described. It involves the sequence of epoxidation, cleavage of the oxirane ring by HI, acetylation, oxidative replacement of iodine by hydroxyl and alkaline hydrolysis (I → VI) without purification of the intermediates. The presence of a 6-keto group does not decrease the yields. The yields are comparable with those obtained by osmylation and the method can find general use, particularly in the synthesis of brassinolide analogs.

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16

Kanavarioti, Anastassia. "False positives and false negatives measure less than 0.001% in labeling ssDNA with osmium tetroxide 2,2’-bipyridine." Beilstein Journal of Nanotechnology 7 (October 12, 2016): 1434–46. http://dx.doi.org/10.3762/bjnano.7.135.

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Osmium tetroxide 2,2’-bipyridine (OsBp) is known to react with pyrimidines in ssDNA and preferentially label deoxythymine (T) over deoxycytosine (C). The product, osmylated DNA, was proposed as a surrogate for nanopore-based DNA sequencing due to OsBp’s “perfect” label attributes. Osmylated deoxyoligos translocate unassisted and measurably slow via sub-2 nm SiN solid-state nanopores, as well as via the alpha-hemolysin (α-HL) pore. Both nanopores discriminate clearly between osmylated and intact nucleobase; α-HL was also shown to discriminate between osmylated T and osmylated C. Experiments presented here confirm that the kinetics of osmylation are comparable for short oligos and long ssDNA and show that pyrimidine osmylation is practically complete in two hours at room temperature with less than 15 mM OsBp. Under the proposed labeling conditions: deoxyoligo backbone degradation measures less than 1/1,000,000; false positives such as osmylated deoxyadenine (A) and osmylated deoxyguanine (G) measure less than 1/100,000; false negatives, i.e., unosmylated C measure less than 1/10,000; and unosmylated T must measure substantially lower than 1/10,000 due to the 27-fold higher reactivity of T compared to C. However, osmylated C undergoes degradation that amounts to about 1–2% for the duration of the labeling protocol. This degradation may be further characterized, possibly suppressed, and the properties of the degradation products via nanopore translocation can be evaluated to assure base calling quality in a DNA sequencing effort.

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17

Willis, Christine L. "Stereoselectivity of osmylation reactions: synthesis of gibberellins A78 and A79." Tetrahedron Letters 31, no. 44 (January 1990): 6437–40. http://dx.doi.org/10.1016/s0040-4039(00)97085-0.

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18

Yang, Jie, Xiangyu Z. Wearing, Philip W. Le Quesne, Jeffrey R. Deschamps, and James M. Cook. "Enantiospecific Synthesis of (+)-Alstonisine via a Stereospecific Osmylation Process(1)." Journal of Natural Products 71, no. 8 (August 2008): 1431–40. http://dx.doi.org/10.1021/np800269k.

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19

Hawkins, J. M., and A. Meyer. "Optically Active Carbon: Kinetic Resolution of C76 by Asymmetric Osmylation." Science 260, no. 5116 (June 25, 1993): 1918–20. http://dx.doi.org/10.1126/science.260.5116.1918.

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20

HAWKINS, J. M., T. A. LEWIS, S. D. LOREN, A. MEYER, J. R. HEATH, Y. SHIBATO, and R. J. SAYKALLY. "ChemInform Abstract: Organic Chemistry of C60 (Buckminsterfullerene): Chromatography and Osmylation." ChemInform 22, no. 26 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199126246.

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21

Narkunan, Kesavaram, and Madhavarao Nagarajan. "Stereochemistry of osmylation of chiral dienes: diastereoselective synthesis of octitols." Journal of the Chemical Society, Chemical Communications, no. 14 (1994): 1705. http://dx.doi.org/10.1039/c39940001705.

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22

Hawkins, Joel M., Axel Meyer, and Michael A. Solow. "Osmylation of C70: reactivity versus local curvature of the fullerene spheroid." Journal of the American Chemical Society 115, no. 16 (August 1993): 7499–500. http://dx.doi.org/10.1021/ja00069a058.

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23

Tserovski, Lyudmil, and Mark Helm. "Diastereoselectivity of 5-Methyluridine Osmylation Is Inverted inside an RNA Chain." Bioconjugate Chemistry 27, no. 9 (September 2016): 2188–97. http://dx.doi.org/10.1021/acs.bioconjchem.6b00403.

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24

Selnick, Harold G., and Samuel J. Danishefsky. "A novel degradation in the avermectin series: A stereospecific osmylation reaction." Tetrahedron Letters 28, no. 42 (January 1987): 4955–58. http://dx.doi.org/10.1016/s0040-4039(00)96668-1.

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25

Wallis, J. M., and Jay K. Kochi. "Direct osmylation of benzenoid hydrocarbons. Charge-transfer photochemistry of osmium tetraoxide." Journal of Organic Chemistry 53, no. 8 (April 1988): 1679–86. http://dx.doi.org/10.1021/jo00243a015.

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26

Hawkins, Joel M. "Osmylation of C60: proof and characterization of the soccer-ball framework." Accounts of Chemical Research 25, no. 3 (March 1992): 150–56. http://dx.doi.org/10.1021/ar00015a008.

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27

Wong, Jerome C. Y., Patrick Lacombe, and Claudio F. Sturino. "A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates." Tetrahedron Letters 40, no. 50 (December 1999): 8751–54. http://dx.doi.org/10.1016/s0040-4039(99)01881-x.

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28

Yu, Libing, Huan Wang, Novruz G. Akhmedov, Christopher Sowa, Kai Liu, Hiyun Kim, and Lawrence Williams. "Direct Entry to 4,10-Didesmethyl (9S)-Dihydroerythronolide A via Catalytic Allene Osmylation." Organic Letters 18, no. 12 (June 7, 2016): 2868–71. http://dx.doi.org/10.1021/acs.orglett.6b01151.

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29

David, Katerine, Cécile Ariente, Alfred Greiner, Jacques Goré, and Bernard Cazes. "Catalytic osmylation of allenic compounds. Synthesis of α-hydroxyketo amino acid precursors." Tetrahedron Letters 37, no. 19 (May 1996): 3335–38. http://dx.doi.org/10.1016/0040-4039(96)00571-0.

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30

Park, Christine Y., B. Moon Kim, and K. Barry Sharpless. "Catalytic osmylation of conjugated dienes: a one-pot stereoselective synthesis of polyols." Tetrahedron Letters 32, no. 8 (February 1991): 1003–6. http://dx.doi.org/10.1016/s0040-4039(00)74472-8.

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31

Annunziata, Rita, Mauro Cinquini, Franco Cozzi, Laura Raimondi, and Angelo Restelli. "Stereoselective Synthesis of Masked Amino-polyolsvia Osmylation of 4,5-Dihydro-5-vinylisoxazoles." Helvetica Chimica Acta 68, no. 5 (August 14, 1985): 1217–25. http://dx.doi.org/10.1002/hlca.19850680518.

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32

NARKUNAN, K., and M. NAGARAJAN. "ChemInform Abstract: Stereochemistry of Osmylation of Chiral Dienes: Diastereoselective Synthesis of Octitols." ChemInform 25, no. 49 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199449240.

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33

Sames, Dalibor, and Robin Polt. "Piperidine Triols via Enantioselective Alkylation and Osmylation of Alanine Schiff Base Esters." Synlett 1995, SI (June 1995): 552–54. http://dx.doi.org/10.1055/s-1995-5282.

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34

Jarosz, Slawomir. "Preparation of higher-carbon sugars by stereoselective osmylation of related allylic alcohols." Carbohydrate Research 224 (February 1992): 73–81. http://dx.doi.org/10.1016/0008-6215(92)84094-9.

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35

Panek, James S., and Pier F. Cirillo. ".pi.-Facial selectivity in catalytic osmylation reactions of chiral C1-oxygenated allylic silanes." Journal of the American Chemical Society 112, no. 12 (June 1990): 4873–78. http://dx.doi.org/10.1021/ja00168a037.

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36

Annunziata, Rita, Mauro Cinquini, Franco Cozzi, and Laura Raimondi. "Double asymmetric induction in the osmylation of -γ-alkoxy-α,β-unsaturated esters." Tetrahedron 44, no. 22 (January 1988): 6897–902. http://dx.doi.org/10.1016/s0040-4020(01)86219-0.

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37

Hanson, James R., Peter B. Hitchcock, Paul B. Reese, and Almaz Truneh. "Stereochemistry of hydroboronation and osmylation of 3α,5-cycloandrost-6-en-17-one." J. Chem. Soc., Perkin Trans. 1, no. 6 (1988): 1465–68. http://dx.doi.org/10.1039/p19880001465.

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38

Broom, Nigel, Peter J. O'Hanlon, Thomas J. Simpson, Rosamund Stephen, and Christine L. Willis. "Studies on the stereoselectivity of osmylation of cis-bicyclo [3.3.0]-oct-6-enes." Journal of the Chemical Society, Perkin Transactions 1, no. 24 (1995): 3067. http://dx.doi.org/10.1039/p19950003067.

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39

Motherwell, William B., and Alvin S. Williams. "Catalytic Photoinduced Charge-Transfer Osmylation: A Novel Pathway from Arenes to Cyclitol Derivatives." Angewandte Chemie International Edition in English 34, no. 18 (October 2, 1995): 2031–33. http://dx.doi.org/10.1002/anie.199520311.

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40

Brimacombe, John S., and Abul K. M. S. Kabir. "The synthesis of some seven-carbon sugars via the osmylation of olefinic sugars." Carbohydrate Research 150, no. 1 (August 1986): 35–51. http://dx.doi.org/10.1016/0008-6215(86)80004-0.

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41

TANG, ZI-RONG. "FACILE CYCLOADDITION OF TRANSITION METAL OXIDES ONTO THE SIDEWALL OF BORON-DOPED FULLERENE." Surface Review and Letters 16, no. 04 (August 2009): 525–32. http://dx.doi.org/10.1142/s0218625x09013025.

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The viability of facile oxidation and cycloaddition of fullerene C 60 with ruthenium tetraoxide ( RuO 4) has been confirmed by means of density functional theory calculations. Owing to the powerful capability of RuO 4 as an oxidant, the addition process has been found to occur readily in the absence of organic base as a catalyst, which is in remarkable contrast to the base-catalyzed osmylation of C 60 with osmium tetraoxide ( OsO 4). Significantly, we have found that boron can be employed as an effective promoter for enhancing the cycloaddition and complexation of transition metal oxides, e.g. RuO 4 and OsO 4, with C 60, in which the base is not needed at all. Our results suggest that boron doping into the lattice of fullerenes and carbon nanotubes would provide a well-defined approach for anchoring transition metal oxides.

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42

Armstrong, Robert W., John E. Tellew, and Edmund J. Moran. "Mono-osmylation of dehydroamino acid dienes: synthesis of dehydroamino acids related to the azinomycins." Tetrahedron Letters 37, no. 4 (January 1996): 447–50. http://dx.doi.org/10.1016/0040-4039(95)02195-7.

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43

Jørgensen, Karl Anker. "A mechanistic approach to the asymmetric epoxidation of allylic alcohols and osmylation of alkenes." Tetrahedron: Asymmetry 2, no. 7 (January 1991): 515–32. http://dx.doi.org/10.1016/s0957-4166(00)86105-4.

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44

Zheng, Tao, Judith Flippen-Anderson, Peng Yu, Tao Wang, Rajaa Mirghani, and James M. Cook. "Stereocontrolled Conversion of Quinine into 10(R),11-Dihydroxydihydroquinine via the Sharpless Osmylation Process." Journal of Organic Chemistry 66, no. 4 (February 2001): 1509–11. http://dx.doi.org/10.1021/jo0015321.

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45

Popescu, Anne, Anna-Britta Hörnfeldt, Salo Gronowitz, and Nils Gunnar Johansson. "Catalytic Osmylation and Antiviral Activity of Some Garbocyclic 5-Substituted Uridine and Cytidine Analogues." Nucleosides and Nucleotides 14, no. 8 (October 1995): 1639–57. http://dx.doi.org/10.1080/15257779508009746.

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46

Evans, David A., and Stephen W. Kaldor. "The stereoselective osmylation of 1,1-disubstituted olefins. Effect of allylic substituents on reaction diastereoselectivity." Journal of Organic Chemistry 55, no. 6 (March 1990): 1698–700. http://dx.doi.org/10.1021/jo00293a004.

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47

Lorsbach, Beth A., Alfred Prock, and Warren P. Giering. "Exploring Stereoselectivity through the Quantitative Analysis of Ligand Effects. Osmylation of Chiral (Acetoxyallyl)silanes." Organometallics 14, no. 4 (April 1995): 1694–99. http://dx.doi.org/10.1021/om00004a025.

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48

Wong, Jerome C. Y., Patrick Lacombe, and Claudio F. Sturino. "ChemInform Abstract: A Ring Closing Metathesis-Osmylation Approach to Oxygenated Oxepanes as Carbohydrate Surrogates." ChemInform 31, no. 8 (June 10, 2010): no. http://dx.doi.org/10.1002/chin.200008195.

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49

DAVID, K., B. CAZES, and J. GORE. "ChemInform Abstract: Synthesis of (.+-.)-5-Hydroxy-4-oxonorvaline by Osmylation of a Functionalized Alkene." ChemInform 28, no. 12 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199712196.

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50

JAROSZ, S. "ChemInform Abstract: Preparation of Higher-Carbon Sugars by Stereoselective Osmylation of Related Allylic Alcohols." ChemInform 23, no. 27 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199227266.

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