Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation–oxa-Michael reactions with unactivated ketones?
Organic & Biomolecular Chemistry Pub Date: 2015-11-02 DOI: 10.1039/C5OB02094H
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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