1,2-: Cis -Selective glucosylation enabled by halogenated benzyl protecting groups
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
Njeri, D., Pertuit, C., & Ragains, J. (2020). 1,2-: Cis -Selective glucosylation enabled by halogenated benzyl protecting groups. Organic and Biomolecular Chemistry, 18 (13), 2405-2409. https://doi.org/10.1039/d0ob00373e