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.
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.
Agoston
Károly
K
Glycom A/S, Technical University of Denmark, Kgs. Lyngby, Denmark. ka@glycom.dk
Dékány
Gyula
G
Lundt
Inge
I
D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D005632:Fructose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013402:Sugar Alcohols / Q000737:chemistry*
C096719:1,5-anhydrotagatose; D004187:Disaccharides; D013402:Sugar Alcohols; D005632:Fructose; C048927:1,5-anhydrofructose