Benzyne-Promoted, 1,2--Selective -Glycosylation with Benzylchalcogenoglycoside Donors.

Org Lett

Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70806, United States.

Published: December 2023

Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2--selective -glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a productive reaction, and unusual protecting groups, auxiliary groups, and additives are avoided.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10696609PMC
http://dx.doi.org/10.1021/acs.orglett.3c03502DOI Listing

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