Title

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

Document Type

Article

Publication Date

4-7-2020

Abstract

This journal is © The Royal Society of Chemistry. 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.

Publication Source (Journal or Book title)

Organic and Biomolecular Chemistry

First Page

2405

Last Page

2409

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