(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → Diacetone-D-glucose

To 250 ml of acetone were added 10.0 g of D-glucose and 125 mg of anhydrous cupric chloride, and the mixture was stirred for 9 hours under reflux in a warm-water bath at 57° to 58° C. The refluxing solvent was continuously dried with 20 g of molecular sieves 3A which was placed between the reaction vessel and the cooling tube. After the conclusion of the reaction, a small amount of aqueous sodium hydrogencarbonate was added to the reaction mixture, and the acetone was distilled off under reduced pressure. The residue was dissolved in benzene, and the benzene solution was washed with aqueous sodium hydrogencarbonate and water, and dried over anhydrous magnesium sulfate. When the benzene was distilled off under reduced pressure, there was obtained 12.4 g (86%) of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (purity of not less than 97%). The compound, when recrystallized from a solvent mixture of chloroform-hexane (1:2), showed a melting point of 107° to 109° C.

1. temperatureunder reflux in
2. temperaturea warm-water bath at 57° to 58° C
3. dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieves 3A which
4. customAfter the conclusion of the reaction
5. distillationthe acetone was distilled off under reduced pressure
6. dissolutionThe residue was dissolved in benzene
7. washthe benzene solution was washed with aqueous sodium hydrogencarbonate and water
8. dry with materialdried over anhydrous magnesium sulfate
9. distillationWhen the benzene was distilled off under reduced pressure

ORD record

ord-37ffdc9c54a448fbaaf81c2b26b591d7

Source dataset

uspto-grants-1984_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04460767