Next Article in Journal
Towards a Synthesis of Vigabatrin Using Glycal Chemistry
Previous Article in Journal
Triisobutylaluminium (TIBAL) Promoted Rearrangement of C-glycosides
Article Menu

Export Article

Open AccessArticle
Molecules 2005, 10(8), 859-870;

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 / Revised: 13 October 2004 / Accepted: 15 October 2004 / Published: 31 August 2005
Full-Text   |   PDF [98 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: (2; 3-Unsaturated-glycopyranosyl)benzene; epoxidation; cis-hydroxylation. (2; 3-Unsaturated-glycopyranosyl)benzene; epoxidation; cis-hydroxylation.

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

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

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top