1,2-O-Trichloroethylidene acetal group protected 3,5-dieno-1,4-furanose derivatives

Yenil N., Yüceer L.

Carbohydrate Research, vol.338, no.19, pp.2013-2016, 2003 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 338 Issue: 19
  • Publication Date: 2003
  • Doi Number: 10.1016/s0008-6215(03)00337-9
  • Journal Name: Carbohydrate Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2013-2016
  • Keywords: Chloralose, Cyclic acetals, Trichloroethylidene acetals, Unsaturated sugar derivatives
  • Manisa Celal Bayar University Affiliated: Yes

Abstract

The preparation of 3,5-(E)-dieno-3,5,6,8-tetradeoxy-(S)-1,2-O-trichloroethylidene-α -D-glycero-octo-1,4-furano-7-ulose starting from either 1,2-O-(S)-trichloroethylidene-α-D-glucofuranose (β-chloralose) or 1,2-O-(S)-trichloroethylidene-α-D-galactofuranose (galactochloralose) and the preparation of methyl 3,5-(E)-dieno-3,5,6-trideoxy-(S)-1,2-O-trichloroethylidene-α -D-glycero-hepta-1,4-furano-uronate starting from β-chloralose are described. Endocyclic double bond formations were realised by the elimination of 3-acetoxy groups using DMF-sodium bicarbonate. This elimination was not successful when the starting compound was 1,2-O-(R)-trichloroethylidene-α -D-glucofuranose (α-chloralose), where the trichloromethyl group occupies the endo position. © 2003 Elsevier Ltd. All rights reserved.