The Wittig-cyclization procedure: acid promoted intramolecular formation of 3-C-branched-chain 3,6-anhydro furano sugars via 2'-oxopropylene derivatives

Carbohydr Res. 2007 Jun 11;342(8):1091-5. doi: 10.1016/j.carres.2007.02.021. Epub 2007 Feb 24.

Abstract

Some olefinic Wittig products, 3-deoxy-5,6-O-isopropylidene-3-C-(2'-oxopropylene)-1,2-O-alkylidene hexofuranose derivatives were converted to the branched-chain 3,6-anhydro-3-C-(2'-oxopropyl) derivatives on treatment with ion exchange resin Amberlite 120 (H(+)) in methanol-water at room temperature. Hydrolysis of 5,6-isopropylidene groups and intramolecular ring-closures took place in one pot reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes*
  • Anhydrides
  • Furans / chemistry*
  • Glucose / chemistry
  • Hexoses / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation

Substances

  • Alkenes
  • Anhydrides
  • Furans
  • Hexoses
  • gulose
  • propylene
  • Glucose