Synthesis of the tetrasaccharide alpha-D-Glcp-(1-->3)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp recognized by calreticulin/calnexin

Carbohydr Res. 2005 Nov 21;340(16):2558-62. doi: 10.1016/j.carres.2005.09.001. Epub 2005 Sep 19.

Abstract

The title compound as its methyl glycoside was efficiently synthesized using a block synthesis approach. Halide-assisted glycosidations between 6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl iodide and ethyl 2-O-acetyl-4,6-di-O-benzyl-1-thio-alpha-D-mannopyranoside using triphenylphosphine oxide as promoter yielded, with complete alpha-selectivity, a disaccharide building block in high yield. The perbenzylated derivative of this proved to be an excellent donor affording 88% of the protected target tetrasaccharide in an NIS/AgOTf-promoted coupling to a known methyl dimannoside acceptor. Deprotection through catalytic hydrogenolysis then gave the target compound in 47% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calnexin / chemistry*
  • Calnexin / metabolism
  • Calreticulin / chemistry*
  • Calreticulin / metabolism
  • Carbohydrate Sequence
  • Catalysis
  • Molecular Sequence Data
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry*
  • Oligosaccharides / metabolism
  • Thioglycosides / chemical synthesis
  • Thioglycosides / chemistry

Substances

  • Calreticulin
  • Oligosaccharides
  • Thioglycosides
  • Calnexin