Benzoyl chloride → HCID 86747468, compound

Participants

Reaction Conditions

Reaction Steps

To about 1 g of crude methyl 6-O-benzoyl-4-deoxy-α,β-D-fructofuranoside (prepared as described in Example 1, Step 6) in dichloromethane (25 mL) containing 4 Å molecular sieves and pyridine (0.28 mL) and maintained at -40° C., benzoyl chloride (0.4 mL) was added and the solution was stirred between -30° to -20° C. for 5 h. The reaction mixture was filtered, diluted with dichloromethane and washed with ice cold 0.5M HCl, sat. aqueous NaHCO3 solution, dried over magnesium sulfate and evaporated. Final purification was effected by chromatography on a column of silica gel. The yields of the separated anomers were 0.582 g of methyl 4-deoxy-1,6-di-O-benzoyl-α-D-fructofuranoside and 0.200 g of methyl 4-deoxy-1,6-di-O-benzoyl-β-D-fructofuranoside.

Provenance & Evidence