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Molecules 2005, 10(8), 859-870; doi:10.3390/10080859

Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides

Laboratoire de Synthèse Asymétrique, CPE Lyon, Université Claude Bernard Lyon 1, France
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Received: 1 October 2004 / Revised: 13 October 2004 / Accepted: 15 October 2004 / Published: 31 August 2005
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Abstract

Epoxidation and cis-hydroxylation of C-phenyl-∆2,3-glycopyranosides have beencarried out with a view to developing C-aryl glycoside synthesis. Epoxidation of (2,3- and (6-O-tert-butyldimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzenedideoxy-D-erythro-hex-2-enopyranosyl)benzene gave predominantly the allo-adductswhatever the configuration at the anomeric center. Epoxidation of (4,6-di-O-tert-butyl-dimethylsilyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)benzene gave the manno- andallo-adducts in a 89:11 and 40:60 ratios for the α- and β-anomers, respectively.Hydroxylation of α-C-phenyl-∆2,3-glycopyranosides using OsO4 afforded the manno-adductonly, whatever the substituents at positions 4 and 6, whereas hydroxylation of (2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)benzene and (4,6-di-O-tert-butyldimethylsilyl-2,3-dideoxy- β-D-erythro-hex-2-enopyranosyl)benzene gave the manno- and allo-adducts in25:75 and 80:20 ratios, respectively.
Keywords: (2; 3-Unsaturated-glycopyranosyl)benzene; epoxidation; cis-hydroxylation. (2; 3-Unsaturated-glycopyranosyl)benzene; epoxidation; cis-hydroxylation.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Fakha, G.; Sinou, D. Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides. Molecules 2005, 10, 859-870.

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