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 journalArticle

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

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Glycosylation
Cations
Ions
chemistry
cations
Thioglycosides
ions
electrochemical oxidation
Electrochemical oxidation
Anodic oxidation
oxidation
Temperature

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry. / Suzuki, Shinkiti; Matsumoto, Kouichi; Kawamura, Kohsuke; Suga, Seiji; Yoshida, Jun Ichi.

In: Organic Letters, Vol. 6, No. 21, 14.10.2004, p. 3755-3758.

Research output: Contribution to journalArticle

Suzuki, Shinkiti ; Matsumoto, Kouichi ; Kawamura, Kohsuke ; Suga, Seiji ; Yoshida, Jun Ichi. / Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry. In: Organic Letters. 2004 ; Vol. 6, No. 21. pp. 3755-3758.
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