Pyridine → HCID 12114363, compound

Participants

Reaction Steps

To a solution of methyl 6-O-(t-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-3-O-allyl-1-thio-β-D-galactopyranosidee (30) (1.4 g, 2.3 mmol) in pyridine (30 mL) was added acetic anhydride (20 g, 196 mmol) in one portion. The resulting solution was left to stir at room temperature for 72 h. The reaction contents were then evaporated to dryness and there residue was dissolved in dichloromethane (200 mL). The solution was washed with potassium hydrogen sulphate solution (1 M×2×50 mL) followed by saturated sodium chloride (150 mL), dried over MgSO4 and evaporated to dryness. The crude residue was purified by chromatography using dichloromethane as the mobile phase to give Methyl 6-O-(t-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-3-O-allyl-4-O-acetyl-1-thio-β-D-galactopyranoside (31)(750 mg, 48%) as a pale yellow oil.

Provenance & Evidence