β-Glycosyl Trifluoroborates as Precursors for Direct α-C-Glycosylation: Synthesis of 2-Deoxy-α- C-glycosides

Daiki Takeda, Makoto Yoritate, Hiroki Yasutomi, Suzuka Chiba, Takahiro Moriyama, Atsushi Yokoo, Kazuteru Usui, Go Hirai

Research output: Contribution to journalArticlepeer-review

Abstract

C-Glycosides are metabolically stable mimics of natural O-glycosides and are expected to be useful tools for investigation of the biological functions of glycans. Here, we describe the synthesis of a series of aryl and vinyl C-glycosides by stereoinvertive sp3-sp2 cross-coupling reactions of 2-deoxyglycosyl boronic acid derivatives with aryl or vinyl halide, mediated by a photoredox/nickel dual catalytic system. Hydrogenation of the vinyl C-glycosides afforded C-linked 2′-deoxydisaccharide analogues.

Original languageEnglish
JournalOrganic letters
DOIs
Publication statusAccepted/In press - 2021

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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