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

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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

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Supplementary files

Article information


Submitted
19 Feb 2020
Accepted
10 Mar 2020
First published
10 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Communication

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, Advance Article , DOI: 10.1039/D0OB00373E

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