Syntheses of monohydroxy benzyl ethers of polyols: tri-O-benzylpentaerythritol and other highly benzylated derivatives of symmetrical polyols

Carbohydr Res. 2004 Oct 20;339(15):2607-10. doi: 10.1016/j.carres.2004.08.006.

Abstract

Symmetrical polyols can be converted into benzyl ethers with one free hydroxyl group in good yield by reaction of the monodibutylstannylene acetal with excess benzyl bromide in the presence of tetrabutylammonium bromide and diisopropylethylamine in xylene. The reaction pathway involves initial benzylation of the dibutylstannylene acetal to give benzyl and bromodibutylstannyl ethers; if a hydroxyl group remains unsubstituted, the latter ether ring closes and reacts further.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis
  • Erythritol
  • Polymers / chemical synthesis*

Substances

  • Benzene Derivatives
  • Polymers
  • polyol
  • Erythritol