Issue 44, 2017

Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

Abstract

A method for activation of unprotected ceramides towards stereo- and site-selective glycosylation is described. Two-point binding of a diarylborinic acid catalyst to the ceramide accelerates its reactions with ‘armed’ glycosyl methanesulfonate donors, resulting in the formation of a β-glycosidic linkage at the primary OH group.

Graphical abstract: Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

Supplementary files

Article information

Article type
Communication
Submitted
03 Mar 2017
Accepted
09 May 2017
First published
16 May 2017

Chem. Commun., 2017,53, 5978-5980

Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

K. A. D’Angelo and M. S. Taylor, Chem. Commun., 2017, 53, 5978 DOI: 10.1039/C7CC01673E

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