Affiliation:
1. Graduate School of Pharmaceutical Sciences, Kyushu University
2. Faculty of Pharmacy, Keio University
Abstract
AbstractC-Glycoside analogues of native glycans are useful molecular tools for medicinal chemistry and chemical biology due to their resistance to cellular glycoside hydrolases. We previously reported an α-selective direct C-glycosylation of 2-deoxy-β-glycosyl boronate through a Ni/photoredox-catalyzed stereoinvertive cross-coupling reaction. Here we report a complementary stereoretentive synthetic method for the preparation of β-C-glycosides from a similar boronate precursor through the addition of a C(sp2) anion followed by 1,2-migration of the glycosyl donor.
Funder
Japan Agency for Medical Research and Development
Japan Society for the Promotion of Science
Mizutani Foundation for Glycoscience
Sumitomo Foundation
Cited by
2 articles.
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