Facile synthesis of per-O-tert-butyldimethylsilyl-beta-D-galactofuranose and efficient glycosylation via the galactofuranosyl iodide

J Org Chem. 2009 Mar 6;74(5):1994-2003. doi: 10.1021/jo8025274.

Abstract

The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4beta) as a new precursor of D-Gal f units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Galactose / analogs & derivatives*
  • Galactose / chemical synthesis
  • Galactose / chemistry*
  • Glycosylation
  • Hydrocarbons, Iodinated / chemistry*
  • Organosilicon Compounds / chemical synthesis*
  • Organosilicon Compounds / chemistry
  • Stereoisomerism

Substances

  • Hydrocarbons, Iodinated
  • Organosilicon Compounds
  • per-O-tert-butyldimethylsilyl-beta-D-galactofuranose
  • Galactose