Issue 13, 2020

1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups

Abstract

We report on our initial results from a systematic effort to implement electron-withdrawing protecting groups and Lewis basic solvents/additives as an approach to 1,2-cis(α)-selective O-glucosylation. 1,2-cis-Selective O-glucosylations are reported with thioglucosides and glucosyl trichloroacetimidates and a range of acceptors. A correlation between electron-withdrawing effects and 1,2-cis selectivity has been established. This phenomenon may prove to be broadly applicable in the area of chemical O-glycosylation.

Graphical abstract: 1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups

Supplementary files

Article information

Article type
Communication
Submitted
19 févr. 2020
Accepted
10 mars 2020
First published
10 mars 2020

Org. Biomol. Chem., 2020,18, 2405-2409

Author version available

1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups

D. K. Njeri, C. J. Pertuit and J. R. Ragains, Org. Biomol. Chem., 2020, 18, 2405 DOI: 10.1039/D0OB00373E

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