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Issue 83, 2019
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2-O-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

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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.

Graphical abstract: 2-O-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

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Article information


Submitted
13 Sep 2019
Accepted
24 Sep 2019
First published
25 Sep 2019

This article is Open Access

Chem. Commun., 2019,55, 12543-12546
Article type
Communication

2-O-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

J. Weber, D. Svatunek, S. Krauter, G. Tegl, C. Hametner, P. Kosma and H. Mikula, Chem. Commun., 2019, 55, 12543
DOI: 10.1039/C9CC07194F

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