Borinic acid-catalyzed stereo- and site-selective synthesis of β-glycosylceramides. Issue 44 (16th May 2017)

• Record Type: Journal Article
• Authors: D'Angelo, Kyan A.; Taylor, Mark S.
• Is Part Of: Chemical communications. Volume 53:Issue 44(2017)
• Page Start: 5978
• Page End: 5980
• Publication Date: 2017-05-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc01673e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Diphenylborinic acid catalysis enables the direct, stereo- and site-selective coupling of glycosyl donors with ceramide lipids. The β-1, 1′-linkages accessed through this method are characteristic of mammalian glycosphingolipids that play diverse roles in physiology, human health and disease. 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.