Highly β-selective mannosylation towards Manβ1-4GlcNAc synthesis: TMSB(C6F5)4 as a Lewis acid/cation trap catalyst

Shin Ichi Tanaka, Mamoru Takashina, Hiroomi Tokimoto, Yukari Fujimoto, Katsunori Tanaka, Koichi Fukase

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Highly β-selective mannosylation of 4,6-0-benzylidene-mannopyranosyl- N-phenyltrifluoroacetimidate (α/β, 5:95, 93% yield) has been realized by utilizing a dual Lewis acid/cation trap catalyst, TMSB(C6F 5)4. The obtained Manβ1-4GlcNTroc unit can be readily converted to a variety of N-linked oligosaccharides.

Original languageEnglish
Pages (from-to)2325-2328
Number of pages4
JournalSynlett
Issue number15
DOIs
Publication statusPublished - 2005 Sep 19
Externally publishedYes

Keywords

  • Lewis acid
  • Manβ1-4GlcNAc synthesis
  • Oligosaccharides
  • Stereoselective mannosylation
  • TMSB(CF)
  • β-glycoside

ASJC Scopus subject areas

  • Organic Chemistry

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