Next Article in Journal
Towards a Synthesis of Vigabatrin Using Glycal Chemistry
Previous Article in Journal
Triisobutylaluminium (TIBAL) Promoted Rearrangement of C-glycosides
Molecules 2005, 10(8), 859-870; doi:10.3390/10080859

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

 and *
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
View Full-Text   |   Download PDF [98 KB, uploaded 18 June 2014]   |   Browse Figures


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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

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

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


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