Methanol → HCID 131720316, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,3R,4E)-3-benzoyloxy-2-azido-1-(4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene prepared as described in Example 1-E (0.422 g, 0.51 mmol) in pyridine (12 mL) and methylene chloride (12 mL) was treated with benzoyl chloride (80 μL, 0.69 mmol) at -15° C. The mixture was stirred for 30 minutes at -15° C. then methanol (10 mL) was added and the mixture was stirred for another 18 hours at room temperature. The solvents were evaporated and the residue was co-evaporated with toluene (2×5 mL) and diluted with ethyl acetate (100 mL). This organic phase was washed with 1M aqueous sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (2×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (60g, 5 to 20% ethyl acetate/hexane) and afforded the title compound (0.420 g, 90%) along with (2S,3R,4E)-3-benzoyloxy-2-azido-1-(2,3-di-O-benzoyl-4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene (0.028g).

Provenance & Evidence