Novel autoxidation and Michael addition of a butenolide-containing sugar leading to a C-branched-chain glucopyranosidulose, and X-ray structure of intermediates

Carbohydr Res. 2003 Aug 12;338(17):1737-43. doi: 10.1016/s0008-6215(03)00257-x.

Abstract

A butenolide-containing sugar available from the aldol condensation of methyl 4,6-O-benzylidene-alpha-D-glucopyranosid-2-ulose with diethyl malonate is autoxidized at the C-3 position into the corresponding alpha,beta-unsaturated gamma-lactone sugar by air, which subsequently undergoes 1,4-conjugate (Michael) addition of hydroxide ion (or water) leading to a C-branched-chain glucopyranosidulose. The autoxidations are also performed in weakly basic, neutral and weakly acidic medium, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • Carbohydrate Conformation
  • Crystallography, X-Ray
  • Furans / chemistry*
  • Glucose / chemistry
  • Glycosides / chemical synthesis*
  • Hydrogen Bonding
  • Ketoses / chemistry
  • Malonates / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Furans
  • Glycosides
  • Ketoses
  • Malonates
  • butenolide
  • Glucose
  • 4-Butyrolactone
  • diethylmalonic acid