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

Chem Commun (Camb). 2017 May 30;53(44):5978-5980. doi: 10.1039/c7cc01673e.

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.