Transition-Metal-Free β-Selective C-Glycosylation of β-Glycosyl Boronates via Stereoretentive 1,2-Migration

Hiroki Yasutomi, Daiki Takeda, Makoto Yoritate, Shuhei Higashibayashi, Takeshi Sugai, Go Hirai

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

C-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.

Original languageEnglish
Pages (from-to)347-352
Number of pages6
JournalSynlett
Volume34
Issue number4
DOIs
Publication statusPublished - Mar 1 2023

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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