1,2-O-Trichloroethylidene acetal group protected 3,5-dieno-1,4-furanose derivatives.
The preparation of 3,5-(E)-dieno-3,5,6,8-tetradeoxy-(S)-1,2-O-trichloroethylidene-alpha-D-glycero-octo-1,4-furano-7-ulose starting from either 1,2-O-(S)-trichloroethylidene-alpha-D-glucofuranose (beta-chloralose) or 1,2-O-(S)-trichloroethylidene-alpha-D-galactofuranose (galactochloralose) and the preparation of methyl 3,5-(E)-dieno-3,5,6-trideoxy-(S)-1,2-O-trichloroethylidene-alpha-D-glycero-hepta-1,4-furano-uronate starting from beta-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-alpha-D-glucofuranose (alpha-chloralose), where the trichloromethyl group occupies the endo position.
D000080:Acetals / Q000737:chemistry*; D015394:Molecular Structure; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*
C484804:3,5-(E)-dieno-3,5,6,8-tetradeoxy-(S)-1,2-O-trichloroethylidene-alpha-D-glycero-octo-1,4-furano-7-ulose; D000080:Acetals; D013402:Sugar Alcohols