Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides

Carbohydr Res. 2003 Feb 14;338(5):447-9. doi: 10.1016/s0008-6215(02)00481-0.

Abstract

A simple and efficient method is developed for the chemoselective one-pot conversion of ethers (benzyl, TBDMS and acetal) to the corresponding benzoates by zinc triflate-catalyzed deprotection and benzoylation by benzoyl bromide. In the same reaction, methyl or p-methoxyphenyl glycosides are converted into glycosyl bromides that are useful in glycosylation reactions.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzoates / chemical synthesis*
  • Benzoates / chemistry*
  • Ether / chemistry*
  • Mesylates / chemistry*

Substances

  • Benzoates
  • Mesylates
  • Ether
  • benzoyl bromide
  • trifluoromethanesulfonic acid