Methanol → HCID 86751609, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,3R,4E)-2-azido-3-benzoyloxy-1-(4,6-di-O-tert-butyloxycarbonylmethyl-β-D-galactopyranosyloxy)-4-octadecene described in Example 15-A (1.34 g 1.63 mmol) in a mixture of pyridine/methylene chloride (1:1, 70 mL) was treated with benzoyl chloride (210 μL, 1.81 mmol) at -78° C. The mixture was stirred at -78° C. for 1 hour, then methanol (10 mL) was added and the resulting mixture was stirred at 22° C. for 20 more hours. The solvents were evaporated and the residue was dissolved in ethyl acetate (200 mL). This solution was washed with water (4×75 mL), saturated aqueous sodium bicarbonate (2×100 mL) and brine (2×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (150 g, 5 to 50 % ethyl acetate/hexane) and gave the title compound (0.275 g, 20%), along with the starting material (0.839 g, 63%), the 2-benzoate (0.124 g, 8%) and the bis-benzoate (0.030 g, 2%).

Provenance & Evidence