The presence of water improves reductive openings of benzylidene acetals with trimethylaminoborane and aluminium chloride

Carbohydr Res. 2003 Apr 4;338(8):697-703. doi: 10.1016/s0008-6215(03)00015-6.

Abstract

The acidic reagent formed in situ from anhydrous AlCl(3) and H(2)O in 3:1 ratio is much more efficient for the reductive openings of the cyclic benzylidene acetals with Me(3)N x BH(3) in tetrahydrofurane than the AlCl(3) alone. Under proposed conditions, the dioxane-type 4,6-O-bezylidene acetals of hexopyranosides give regioselectively the corresponding 4-hydroxy,6-O-benzyl derivatives in excellent yields. Reductive openings of the dioxolane-type 3,4-O-benzylidene acetals of galactopyranoside are also very efficient and regioselective and give either 3-O-benzyl derivative (from 3,4-O-exo-benzylidene acetal) or 4-O-benzyl derivative (from 3,4-O-endo-benzylidene acetal) depending on the configuration of the acetal carbon atom.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Aluminum Compounds / chemistry*
  • Benzylidene Compounds / chemistry*
  • Boranes / chemistry*
  • Chlorides / chemistry*
  • Hexoses / chemistry
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Acetals
  • Aluminum Compounds
  • Benzylidene Compounds
  • Boranes
  • Chlorides
  • Hexoses
  • Water