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

Chemical Communications : Chem Comm
Kyan A D'Angelo, Mark S Taylor

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.

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Citations

Jul 4, 2018·Chemical Reviews·Michael Martin Nielsen, Christian Marcus Pedersen
Jul 7, 2018·Chemical Reviews·Carmanah D HunterChristopher W Cairo
Dec 7, 2018·Chemical Reviews·Victoria Dimakos, Mark S Taylor
Jan 9, 2019·The Journal of Organic Chemistry·Daniel GorelikMark S Taylor
Dec 8, 2021·Proceedings of the National Academy of Sciences of the United States of America·Blaise Gatin-FraudetBoris Vauzeilles
Dec 1, 2021·Angewandte Chemie·Michael Martin NielsenChristian Marcus Pedersen

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