2-Methyl-6-nitrobenzoic anhydride → HCID 86701314, compound

Participants

Reaction Steps

A solution of (S)-2-(benzyloxycarbonylamino)-3-((2S,3S,4R)-4-hydroxy-2,3,5-tris(2-methylallyloxy)pentyloxy)propanoic acid (400 mg, 0.747 mmol) in anhydrous toluene (400 mL) was added to a solution of MNBA (411 mg, 1.195 mmol) and DMAP (547 mg, 4.48 mmol) in toluene (1600 mL) over the course of 3 h via syringe pump. After the addition was complete, the reaction mixture was stirred for 1 h, concentrated, and the residue purified by flash chromatography (SiO2, 200 EtOAc/hexanes) to furnish benzyl (3S,7S,8R,9R)-7,8-bis(2-methylallyloxy)-9-((2-methylallyloxy)methyl)-2-oxo-1,5-dioxonan-3-ylcarbamate (140 mg, 36%) and (3R,7S,8R,9R)-7,8-bis(2-methylallyloxy)-9-((2-methylallyloxy)methyl)-2-oxo-1,5-dioxonan-3-ylcarbamate as white foams (140 mg, 36%).

Provenance & Evidence