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

Ay K., Çetin F., Yüceer L.

Carbohydrate Research, vol.342, no.8, pp.1091-1095, 2007 (SCI-Expanded, Scopus) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 342 Issue: 8
  • Publication Date: 2007
  • Doi Number: 10.1016/j.carres.2007.02.021
  • Journal Name: Carbohydrate Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1091-1095
  • Keywords: branched-chain sugars, anhydrosugars, Wittig-cyclization, intramolecular ring-closure
  • Manisa Celal Bayar University Affiliated: Yes

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. © 2007 Elsevier Ltd. All rights reserved.