Antimony pentachloride → Diacetone-D-glucose

Temperature

60 °C

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.

1. temperaturethe mixture was refluxed
2. customDuring this reaction
3. dry with materialthe refluxing solvent was dried with 20 g of Molecular Sieves 3A
4. customAfter completion of the reaction, 1.60 g of the starting sugar
5. filtrationwas recovered by filtration
6. additionA small amount of pyridine was then added to the filtrate
7. distillationthe acetone was distilled off under reduced pressure
8. dissolutionThe residue was dissolved in benzene
9. washthe solution was washed with aqueous sodium bicarbonate and water
10. dry with materialdried over anhydrous magnesium sulfate
11. distillationThe benzene was distilled off under reduced pressure

ORD record

ord-d9fa2f9105fd49f3bd1c0d33358897b1

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659809