(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate → 3,3-dimethyl-5,6-bis(nitrooxy)hexyl (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl carbonate

Participants

Reaction Steps

To a solution of (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate (0.962 g, 3.10 mmol) in DCM (40 ml), (prepared as described in EXAMPLE 7, Step C), 6-hydroxy-4,4-dimethylhexane-1,2-diyl dinitrate (0.780, 3.10 mmol) and 4-dimethylaminopyridine (0.379 g, 3.10 mmol) were added and the mixture was stirred at room temperature for 18 hrs. Then the mixture was diluted with DCM and washed with a 5% solution of sodium dihydrogen phosphate (2×30 ml) and brine (1×30 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 20 to 80%), affording the title compound.

Provenance & Evidence