Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

Noriyasu Hada, Junko Oka, Ayaka Nishiyama, Tadahiro Takeda

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An α-selective galactosylation was demonstrated under various conditions. Among these α-galactoside approaches, high α-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsilylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species.

Original languageEnglish
Pages (from-to)6647-6650
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number37
DOIs
Publication statusPublished - 2006 Sep 11

Keywords

  • 1,2-cis-Glycoside
  • Di-tert-butylsilylene group
  • Zygomycetes species
  • d-Galactose
  • α-Galactosylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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