Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation–oxa-Michael reactions with unactivated ketones. Issue 1 (13th November 2015)

• Record Type: Journal Article
• Authors: Johnson, Sherida; Tanaka, Fujie
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 1(2016)
• Page Start: 259
• Page End: 264
• Publication Date: 2015-11-13
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02094h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : C-glycosides were synthesized from unprotected 2- N -acyl-aldohexoses and unactivated ketones in one pot via aldol condensation–oxa-Michael reactions. Abstract : C-glycosides are important compounds as they are used as bioactive molecules and building blocks. We have developed methods to concisely synthesize C-glycosides from unprotected 2- N -acyl-aldohexoses and unactivated ketones; we designed aldol-condensation–oxa-Michael addition reactions catalyzed by amine-based catalysts using additives. Depending on the conditions used, C-glycosides were stereoselectively obtained. Our methods allowed the C–C bond formations at the anomeric centers of unprotected carbohydrates under mild conditions to lead the C-glycosides in atom- and step-economical ways.