Hydrochloric Acid → HCID 86602939, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2,3-di-O-Benzyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside (J. Org. Chem., 2001, 66, 5965-5975) (163.9 g, 310 mmol) was dissolved in methylene chloride (1.5 L), 4-dimethylaminopyridine (43.5 g, 352 mmol) and triethylamine (49.0 mL, 352 mmol) were added thereto and benzoyl chloride (43.2 mL, 372 mmol) was added dropwise thereto under ice-cooling, followed by stirring of the mixture at 0° C. for 1 hour. Diluted hydrochloric acid (2N, 500 mL) was added to the reaction mixture and after the mixture was extracted with methylene chloride (1 L), the organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (1 L) and a saturated aqueous NaCl solution (1 L). After it was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1, V/V) to obtain the desired title compound (196 g, yield: 99%) as a colorless solid.

Provenance & Evidence