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

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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

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Publication details

The article was received on 03 Mar 2017, accepted on 09 May 2017 and first published on 16 May 2017


Article type: Communication
DOI: 10.1039/C7CC01673E
Citation: Chem. Commun., 2017, Advance Article
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    Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides

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

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