4.5 Article

Synthesis of 4-O-glycosylated 1,5-anhydro-D-fructose and of 1,5-anhydro-D-tagatose from a common intermediate 2,3-O-isopropylidene-D-fructose

Journal

CARBOHYDRATE RESEARCH
Volume 344, Issue 8, Pages 1014-1019

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2009.03.005

Keywords

1,5-Anhydro-D-fructose; 1,5-Anhydro-D-tagatose; Glycosylated 1,5-anhydro-D-fructose; Glycosylated 1,5-anhydro-D-tagatose; Chemical synthesis

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Four novel disaccharides of glycosylated 1,5-anhydro-D-ketoses have been prepared: 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-fructose, 1,5-anhydro-4-O-beta-D-glucopyranosyl-D-tagatose, and 1,5-anhydro-4-O-beta-D-galactopyranosyl-D-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-beta-D-fructopyranose, was prepared from D-fructose and was converted into the D-tagatose derivative by oxidation followed by stereoselective reduction to the 4-epimer. The anhydroketoses thus prepared were glycosylated and deprotected to give the disaccharides. (C) 2009 Elsevier Ltd. All rights reserved.

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