由共同中间体2,3-O-异亚丙基-D-果糖合成4-O-糖基化的1,5-脱水-D-果糖和1,5-脱水-D-塔格糖。
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.
作者信息
Agoston Károly, Dékány Gyula, Lundt Inge
机构信息
Glycom A/S, Technical University of Denmark, Kgs. Lyngby, Denmark.
出版信息
Carbohydr Res. 2009 May 26;344(8):1014-9. doi: 10.1016/j.carres.2009.03.005. Epub 2009 Mar 12.
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.
已制备出四种新型的糖基化1,5-脱水-D-酮糖二糖：1,5-脱水-4-O-β-D-吡喃葡萄糖基-D-果糖、1,5-脱水-4-O-β-D-吡喃半乳糖基-D-果糖、1,5-脱水-4-O-β-D-吡喃葡萄糖基-D-塔格糖和1,5-脱水-4-O-β-D-吡喃半乳糖基-D-塔格糖。常见中间体1,5-脱水-2,3-O-异亚丙基-β-D-吡喃果糖由D-果糖制备而成，并通过氧化反应转化为D-塔格糖衍生物，随后立体选择性还原为4-差向异构体。如此制备的脱水酮糖经糖基化和脱保护反应后得到二糖。
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