Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

Shinkiti Suzuki, Kouichi Matsumoto, Kohsuke Kawamura, Seiji Suga, Jun Ichi Yoshida

Research output: Contribution to journalArticlepeer-review

71 Citations (Scopus)

Abstract

(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.

Original languageEnglish
Pages (from-to)3755-3758
Number of pages4
JournalOrganic Letters
Volume6
Issue number21
DOIs
Publication statusPublished - Oct 14 2004
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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