Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′- dideoxynucleosides

Koichi Mitsudo, Takashi Kawaguchi, Seiji Miyahara, Wataru Matsuda, Manabu Kuroboshi, Hideo Tanaka

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the α- or β-thiodideoxyglycosides proceeded smoothly at -78°C to give dideoxynucleosides in a β-selective manner, presumably through a 1-halo-substituted glycosyl donor.

Original languageEnglish
Pages (from-to)4649-4652
Number of pages4
JournalOrganic Letters
Volume7
Issue number21
DOIs
Publication statusPublished - Oct 13 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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