2-O-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation. Issue 83 (2nd October 2019)

• Record Type: Journal Article
• Authors: Weber, Julia; Svatunek, Dennis; Krauter, Simon; Tegl, Gregor; Hametner, Christian; Kosma, Paul; Mikula, Hannes
• Is Part Of: Chemical communications. Volume 55:Issue 83(2019)
• Page Start: 12543
• Page End: 12546
• Publication Date: 2019-10-02
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc07194f
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Benzyloxycarbonyl can be used as participating group for the diastereoselective glycosylation of base-labile products and the synthesis of glycosyl esters. Abstract : By reviving an old idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O -2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1, 2- trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.