Acetic Anhydride → diphenylmethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetraacetoxy-5-(N-benzyloxycarbonyl-L-leucyl)aminohexanoyl]amino-3-phenylpropionate

Participants

Reaction Steps

To a solution of diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (200 mg) in pyridine (5 ml) was added acetic anhydride (3 ml) and the mixture was stirred at room temperature for 4 days. After concentration under reduced pressure, the residue was dissolved in ethyl acetate (100 ml) and washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine respectively. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through silica gel column chromatography, followed by elution with ethyl acetate-hexane (1:1). The effective fractions were combined and concentrated under reduced pressure to afford the title compound (85 mg).

Provenance & Evidence