Antimony pentachloride → Diacetone-D-glucose

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To 200 ml of acetone were added 10.0 g of D-glucose and 149.5 mg of antimony pentachloride, and the mixture was refluxed with stirring in a water bath of 60° C. for 8 hours. During this reaction, the refluxing solvent was dried with 20 g of Molecular Sieves 3A interposed between the reaction vessel and the condenser. After completion of the reaction, 1.60 g of the starting sugar was recovered by filtration. A small amount of pyridine was then added to the filtrate, and the acetone was distilled off under reduced pressure. The residue was dissolved in benzene, and the solution was washed with aqueous sodium bicarbonate and water, and dried over anhydrous magnesium sulfate. The benzene was distilled off under reduced pressure to give 10.46 g (72.4%) of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. The compound, when recrystallized from a mixed solvent of chloroform-n-hexane (1:2), showed a melting point of 107°-109° C.

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