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

Yenil N., Yüceer L.

Carbohydrate Research, cilt.338, sa.19, ss.2013-2016, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 338 Sayı: 19
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1016/s0008-6215(03)00337-9
  • Dergi Adı: Carbohydrate Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2013-2016
  • Anahtar Kelimeler: Chloralose, Cyclic acetals, Trichloroethylidene acetals, Unsaturated sugar derivatives
  • Manisa Celal Bayar Üniversitesi Adresli: Hayır

Özet

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.