Bromodimethylsulfonium bromide/silver triflate-promoted glycosylations using glycosyl allenoates as donors

Carbohydr Res. 2013 Nov 15:381:101-11. doi: 10.1016/j.carres.2013.08.005. Epub 2013 Aug 19.

Abstract

A series of novel glycosyl allenoates were prepared by condensions of hemiacetals with 3,3-dimethyl-4,5-allenoic acid. Their glycosylations with various alcohols under the promotion of bromodimethylsulfonium bromide/silver triflate smoothly proceeded to produce disaccharides. Studies reveal that allenic group is crucial for the efficient glylcosylation of glycosyl allenoate.

Keywords: Bromodimethylsulfonium bromide; Glycosyl allenoate; Glycosylation; Silver triflate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis
  • Alkadienes / chemistry*
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Glycosylation
  • Mesylates / chemistry*
  • Molecular Structure
  • Sulfonium Compounds / chemistry*

Substances

  • Alkadienes
  • Disaccharides
  • Glycosides
  • Mesylates
  • Sulfonium Compounds
  • trifluoromethanesulfonic acid