Highly β-stereoselective glycosylation by use of 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor for synthesis of 2,6-dideoxy-β-glycosides

Kazunobu Toshima, Yuko Nozaki, Satsuki Mukaiyama, Kuniaki Tatsuta

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Gycosylations of the 1-O-acetyl-2,6-anhydro-2-thio sugar 3 with alcohols in the presence of several Lewis acids in CH2Cl2 proceeded smoothly to give the corresponding β-O-glycosides with high stereocontrol in high yields, and the selectivity of the glycosylation was highly independent on Lewis acids.

Original languageEnglish
Pages (from-to)1491-1494
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number11
DOIs
Publication statusPublished - 1992 Mar 10

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Keywords

  • 1-O-acetyl-2,6-anhydro-2-thio glycosyl donor
  • 2,6-dideoxy glycoside
  • Lewis acid
  • thermodynamic control
  • β-stereoselective glycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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