Stereoselective synthesis of a novel Galf-disaccharide mimic: β-d-galactofuranosyl-(1-5)-β-d-galactofuranosyl motif of mycobacterial cell walls

Chunyan Liu, Hong Kang, Richard H Wightman, Shende Jiang

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

A Galf-disaccharide mimic, an analogue of the acceptor substrates of mycobacterial Galf-transferases, was obtained by nucleophilic addition of a L-arabinofurano-alkyne to iminogalactitol-derived nitrone. Remarkably, the nucleophilic addition could be performed highly efficiently and stereoselectively in the presence of diethylzinc in toluene using protected nitrone and alkynyl sugar as reaction partners and thus opens a concise approach to a diversity of disaccharide mimics. (C) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1192-1194
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number10
DOIs
Publication statusPublished - 6 Mar 2013

Keywords

  • Galf-disaccharide mimic
  • Iminogalactitol-derived nitrone
  • L-Arabinofurano-alkyne
  • CYCLOADDITION REACTIONS
  • NITRONE

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