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Issue 1, 2016
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Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation–oxa-Michael reactions with unactivated ketones

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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.

Graphical abstract: Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation–oxa-Michael reactions with unactivated ketones

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Article information


Submitted
09 Oct 2015
Accepted
02 Nov 2015
First published
02 Nov 2015

Org. Biomol. Chem., 2016,14, 259-264
Article type
Paper
Author version available

Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation–oxa-Michael reactions with unactivated ketones

S. Johnson and F. Tanaka, Org. Biomol. Chem., 2016, 14, 259
DOI: 10.1039/C5OB02094H

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