Yenil, NYuceer, L2019-10-272019-10-2720030008-6215https://doi.org/10.1016/S0008-6215(03)00337-9https://hdl.handle.net/11454/36611The preparation of 3.5-(E)-dieno-3,5,6.8-tetracdeoxy-(S)-1,2-O-trichloroethylidene-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)-trichloroethlylidene-alpha-D-glucofuranose (alpha-chloralose), where the trichloromethyl group occupies the endo position. (C) 2003 Elsevier Ltd. All rights reserved.en10.1016/S0008-6215(03)00337-9info:eu-repo/semantics/closedAccesscyclic acetalstrichloroethylidene acetalschloraloseunsaturated sugar derivativesArticle3381920132016WOS:00018530940001114499578Q2Q1