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 |
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Authors: | Károly Agoston Gyula Dékány |
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Institution: | a Glycom A/S, Technical University of Denmark, Building 201, DK-2800 Kgs. Lyngby, Denmark b Department of Chemistry, Technical University of Denmark, Building 201, DK-2800 Kgs. Lyngby, Denmark |
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Abstract: | Four novel disaccharides of glycosylated 1,5-anhydro-d-ketoses have been prepared: 1,5-anhydro-4-O-β-d-glucopyranosyl-d-fructose, 1,5-anhydro-4-O-β-d-galactopyranosyl-d-fructose, 1,5-anhydro-4-O-β-d-glucopyranosyl-d-tagatose, and 1,5-anhydro-4-O-β-d-galactopyranosyl-d-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-β-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. |
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Keywords: | 1 d-fructose" target="_blank">5-Anhydro-d-fructose 1 d-tagatose" target="_blank">5-Anhydro-d-tagatose Glycosylated 1 d-fructose" target="_blank">5-anhydro-d-fructose Glycosylated 1 d-tagatose" target="_blank">5-anhydro-d-tagatose Chemical synthesis |
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