O,O-dimethylthiophosphonosulfenyl bromide-silver triflate: a new powerful promoter system for the preactivation of thioglycosides

Org Biomol Chem. 2011 Jan 21;9(2):616-22. doi: 10.1039/c0ob00380h. Epub 2010 Nov 10.

Abstract

O,O-Dimethylthiophosphonosulfenyl bromide (DMTPSB) in combination with silver triflate provides a powerful thiophilic promoter system. Both "armed" and "disarmed" thioglycoside glycosyl donors can be activated to form glycosidic linkages efficiently by the pre-activation protocol. The usefulness of this new promoter is illustrated by a successful iterative one-pot oligosaccharide assembly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides / chemistry*
  • Glycosylation
  • Mesylates / chemistry*
  • Molecular Structure
  • Oligosaccharides / chemistry
  • Organothiophosphorus Compounds / chemistry*
  • Silver Compounds / chemistry*
  • Thioglycosides / chemistry*

Substances

  • Bromides
  • Mesylates
  • O,O-dimethylthiophosphonosulfenyl bromide-silver triflate
  • Oligosaccharides
  • Organothiophosphorus Compounds
  • Silver Compounds
  • Thioglycosides
  • silver bromide