Synthetic carbohydrate research based on organic electrochemistry

Toshiki Nokami, Kodai Saito, Jun Ichi Yoshida

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Development of a novel method for generating glycosyl cations or their equivalents is highly desired, because such intermediates are crucial for developing stereoselective glycosylations in oligosaccharide syntheses. In this review we focus on electrochemical methods that we have recently developed. The anodic oxidation of thioglycosides is effective for generating glycosyl triflate pools, which react with glycosyl acceptors. The reaction of glycosyl triflate pools with diorganosulfides gives glycosyl sulfonium ions, which also serve as effective glycosylation intermediates. The indirect electrochemical method is effective for the generation of glycosyl cations or their equivalents and the use of a flow-microreactor system enables glycosylation using such intermediates.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalCarbohydrate Research
Volume363
DOIs
Publication statusPublished - 2012 Dec 1
Externally publishedYes

Fingerprint

Glycosylation
Electrochemistry
Carbohydrates
Cations
Thioglycosides
Research
Anodic oxidation
Oligosaccharides
Ions

Keywords

  • Anodic oxidation
  • Glycosyl triflate
  • Glycosylation
  • Oligosaccharide

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Synthetic carbohydrate research based on organic electrochemistry. / Nokami, Toshiki; Saito, Kodai; Yoshida, Jun Ichi.

In: Carbohydrate Research, Vol. 363, 01.12.2012, p. 1-6.

Research output: Contribution to journalArticle

Nokami, Toshiki ; Saito, Kodai ; Yoshida, Jun Ichi. / Synthetic carbohydrate research based on organic electrochemistry. In: Carbohydrate Research. 2012 ; Vol. 363. pp. 1-6.
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