Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

Yasuhiro Meguro, Masato Noguchi, Gefei Li, Shin ichiro Shoda

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

Original languageEnglish
Article number152198
JournalTetrahedron Letters
Volume61
Issue number32
DOIs
Publication statusPublished - 2020 Aug 6
Externally publishedYes

Keywords

  • Glycosyl Bunte salt
  • Glycosyl thiolate
  • One-pot aqueous synthesis
  • S-Glycoside
  • Sodium sulfide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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