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Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides
Laboratoire de Synthèse Asymétrique, CPE Lyon, Université Claude Bernard Lyon 1, France
* Author to whom correspondence should be addressed.
Received: 1 October 2004; in revised form: 13 October 2004 / Accepted: 15 October 2004 / Published: 31 August 2005
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.
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Fakha, G.; Sinou, D. Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides. Molecules 2005, 10, 859-870.
Fakha G, Sinou D. Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides. Molecules. 2005; 10(8):859-870.
Fakha, G.; Sinou, D. 2005. "Epoxidation and Bis-hydroxylation of C-Phenyl-∆2,3-glycopyranosides." Molecules 10, no. 8: 859-870.