Efficient synthesis of core 2 class glycosyl amino acids by one-pot glycosylation approach

Hiroshi Tanaka, Masaatsu Adachi, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

We describe the one-pot synthesis of core 2 class branched oligosaccharides initiated by chemo-selective glycosylation of silyl ether. Glycosylation of 6-O-silyl-4-benzyl-2-azido-thiogalactoside with glycosyl fluoride provided selectively 6-glycosylated thioglycoside without both O-glycosylation at the 3 position and S-glycosylation. Subsequent coupling of galactosyl fluoride and amino acids afforded the protected branched oligosaccharides in good yields.

Original languageEnglish
Pages (from-to)1433-1436
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number7
DOIs
Publication statusPublished - 2004 Feb 9
Externally publishedYes

Keywords

  • Glycopeptides
  • Glycosyl amino acids
  • Glycosyl fluorides
  • Oligosaccharide
  • One-pot glycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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