Practical preparation of 2-azido-2-deoxy-beta-D-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides

Carbohydr Res. 2007 Dec 28;342(18):2810-7. doi: 10.1016/j.carres.2007.09.001. Epub 2007 Sep 7.

Abstract

1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-beta-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-beta-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative O10 antigen from Acinetobacter baumannii, was efficiently synthesized using these derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acinetobacter baumannii / chemistry
  • Carbohydrate Sequence
  • Carbonates / chemical synthesis*
  • Carbonates / chemistry*
  • Hexosamines / chemistry
  • Mannose / analogs & derivatives*
  • Mannose / chemistry*
  • Molecular Sequence Data
  • O Antigens / chemistry
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry*

Substances

  • Carbonates
  • Hexosamines
  • O Antigens
  • Trisaccharides
  • mannosamine
  • Mannose