Academic literature on the topic 'Tetrahydropyrany'

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Journal articles on the topic "Tetrahydropyrany"

1

Chen, Guangwu, Richard W. Franck, Guangli Yang, and Michael Blumenstein. "Anomeric effects of sulfones." Canadian Journal of Chemistry 80, no. 8 (2002): 894–99. http://dx.doi.org/10.1139/v02-095.

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The anomeric effect of the sulfone group in tetrahydropyrans has been determined. The value is >2 kcal mol–1, which is larger than the A-value of a methyl group but less than the A-value of the sulfone in a tetrahydropyran. Hence, in an unsubstituted tetrahydropyranyl sulfone, the equatorial conformer predominates, whereas in a properly substituted methyltetrahydropyranyl sulfone, an axial sulfone is preferred over an axial methyl group.Key words: sulfone, tetrahydropyran, anomeric effect.
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2

di Dio, Philipp J., Stefan Zahn, Christian B. W. Stark, and Barbara Kirchner. "Understanding Selectivities in Ligand-free Oxidative Cyclizations of 1,5- and 1,6-Dienes with RuO4 from Density Functional Theory." Zeitschrift für Naturforschung B 65, no. 3 (2010): 367—s400. http://dx.doi.org/10.1515/znb-2010-0321.

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Quantum-chemical calculations using density functional theory were carried out to investigate the mechanism of the oxidative cyclization of 1,5- and 1,6-dienes with ruthenium tetroxide. Current experimental results show different selectivities for the formation of tetrahydrofuran and tetrahydropyran derivatives. Our theoretical data correctly reproduce the experimental selectivities. Transition structures for the first [3+2]-cycloaddition of RuO4 with ethene and for the second [3+2]- cycloaddition with two ethene molecules, 1,5-hexadiene, and 1,6-heptadiene were calculated. For the formation o
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3

Shouksmith, Andrew E., Laura E. Evans, Deborah A. Tweddle, et al. "Synthesis and Activity of Putative Small-Molecule Inhibitors of the F-Box Protein SKP2." Australian Journal of Chemistry 68, no. 4 (2015): 660. http://dx.doi.org/10.1071/ch14586.

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The tetrahydropyran 4-(((3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline was reported to disrupt the SCFSKP2 E3 ligase complex. Efficient syntheses of this tetrahydropyran derivative and analogues, including the des-dimethyl derivative 4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline, are described. The enantiomers of the des-dimethyl compound were obtained using Evans’ chiral auxiliaries. Structure–activity relationships for these tetrahydropyrans and analogues have been determined by measurement of growth-inhibitory ac
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4

Ryu, Jae-Sang, Yunjeong Park, and Jae Lee. "Synthesis of a Cyclic Analogue of Tuv N-Methyl Tubulysin." Synlett 26, no. 08 (2015): 1063–68. http://dx.doi.org/10.1055/s-0034-1379900.

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Tubulysins are the most potent antimitotic agents known so far. We are interested in the conformational effect of tubulysin and herein we report the design and synthesis of a conformationally rigid cyclic analogue of Tuv N-methyl tubulysin. A conformationally rigid tetrahydropyran moiety was incorporated into the Tuv fragment via enantioselective hetero Diels–Alder reaction to prevent the rotation of the Tuv chain. The following diastereoselective reductive amination yielded the (4-methylamino)tetrahydropyranyl Tuv fragment, which was coupled to d-Mep-l-Ile dipeptide fragment and Tup fragment
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5

Ouedraogo, Adama, and Jean Lessard. "The conformational behaviour of 2-aryloxytetrahydropyrans and 2-acetoxytetrahydropyran, and barrier to ring inversion." Canadian Journal of Chemistry 69, no. 3 (1991): 474–80. http://dx.doi.org/10.1139/v91-071.

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The 13C nuclear magnetic resonance data of a series of 2-(4-substituted-phenoxy)tetrahydropyrans at 156 K and in CF2Br2 and CHFCl2 solvents show that the axial preference increases with electron withdrawal in the aryloxy group: from 79% (ΔG°E→A = −0.4 kcal mol−1) (4-OCH3) to 90% (ΔG°E→A = −0.7 kcal mol−1) (4-NO2) in CF2Br2. The axial preference (anomeric effect) is smaller in the more polar CHFCl2 solvent, as expected, and the substituent effect is smaller also: change in ΔG°E→A from −0.3 (4-OCH3) to −0.5 (4-NO2) kcal mol−1. However, the axial preference of 2-acetoxytetrahydropyran is shown to
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6

Sipilä, Kaija, and Jarno Kansikas. "Structural Features of 2-S-Substituted Crystalline Tetrahydropyrans. Syntheses of 2-(2-Naphthylthiomethylthio)-Tetrahydropyran Derivatives." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 1 (2002): 19–31. http://dx.doi.org/10.1080/10426500210214.

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7

Díez-Poza, Carlos, Patricia Val, Francisco Pulido, and Asunción Barbero. "Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues." Marine Drugs 16, no. 11 (2018): 421. http://dx.doi.org/10.3390/md16110421.

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Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein develope
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8

Clarke, Paul A., Philip B. Sellars, and Nadiah Mad Nasir. "A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones." Organic & Biomolecular Chemistry 13, no. 16 (2015): 4743–50. http://dx.doi.org/10.1039/c5ob00292c.

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New variations of the Maitland–Japp reaction have been developed to enable the synthesis of dihydropyrans and tetrahydropyrans with tertiary and quaternary stereocentres, including the functionalised tetrahydropyrans in Civet and the A-ring of lasonolide A.
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9

Dilworth, J. R., D. V. Griffiths, J. M. Hughes, and S. Morton. "SYNTHESIS OF 2-S-(2-TETRAHYDROPYRANYL)THIOETHYLPHOSPHINES RADICAL ADDITION OF PHOSPHINES TO AND 2-MERCAPTOETHYLPHOSPHINES BY FREE 2-(VINYLTHIO)TETRAHYDROPYRAN." Phosphorus, Sulfur, and Silicon and the Related Elements 71, no. 1-4 (1992): 249–51. http://dx.doi.org/10.1080/10426509208034518.

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10

Lee, Kiyoun, Hyoungsu Kim, and Jiyong Hong. "Stereoselective Synthesis of Tetrahydropyrans through Tandem and Organocatalytic Oxa-Michael Reactions: Synthesis of the Tetrahydropyran Cores of ent-(+)-Sorangicin A." European Journal of Organic Chemistry 2012, no. 5 (2011): 1025–32. http://dx.doi.org/10.1002/ejoc.201101549.

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