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

研究成果: Article査読

2 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)347-352
ページ数6
ジャーナルSynlett
34
4
DOI
出版ステータスPublished - 2023 3月 1

ASJC Scopus subject areas

  • 有機化学

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