Sulfuryl chloride → HCID 54049155, compound

Participants

Reaction Steps

To a solution of crude methyl 6-O-benzyl-2,3-di-O-benzoyl-α-D-glycopyranoside (compound 66) (from previous step) in 300 mL of pyridine at -40° C. was added sulfuryl chloride (15 mL). After 1 hour, the cooling bath was removed and stirring was continued at room temperature for 3 hours. Dichloromethane was then added and the resulting solution was washed with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel, eluting with dichloromethane, to provide methyl 6-O-benzyl-2,3-di-O-benzoyl-4-chloro-4-deoxy-α-D-galactopyranoside (compound 67) (15.3 g, 90.0% --based on compound 65) as a syrup.

Provenance & Evidence