Dimethyl Sulfoxide → (3aR,5R,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (25.16 mL) and dichloromethane (200 mL) were taken in a three-neck round bottom flask and cooled to −75° C. under a nitrogen atmosphere. Then dimethylsulfoxide (27.3 mL) was added drop-wise slowly maintaining the temperature at −70° C. The reaction mixture was stirred for 30 minutes at the same temperature, and then diacetone-α-D-glucose (50 g) in dichloromethane (500 mL) was charged slowly, maintaining the temperature at −70° C. After 20 minutes, triethylamine (80 mL) was added drop-wise to the above mixture at the same temperature. A saturated solution of ammonium chloride in water (500 mL) was charged to the reaction mixture after 30 minutes, and the temperature was allowed to rise to room temperature. The reaction mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the title compound (45 g).

Provenance & Evidence