An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

Carbohydr Res. 2012 Jun 1:354:6-20. doi: 10.1016/j.carres.2012.02.021. Epub 2012 Mar 1.

Abstract

An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetonitriles / chemical synthesis*
  • Acetonitriles / chemistry*
  • Catalysis
  • Ethers / chemistry*
  • Gels / chemistry
  • Mesylates / chemistry
  • Molecular Conformation
  • Silanes / chemistry*
  • Silicon Dioxide / chemistry

Substances

  • Acetonitriles
  • Ethers
  • Gels
  • Mesylates
  • Silanes
  • Silicon Dioxide
  • trifluoromethanesulfonic acid
  • acetonitrile