ClCCl.[N+:4]([O-:18])([O:6][CH2:7][C@H:8]([O:14][N+:15]([O-:17])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:5].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.O>[N+:4]([O-:18])([O:6][CH2:7][C@H:8]([O:14][N+:15]([O-:17])=[O:16])[CH2:9][CH2:10][CH2:11][CH:12]=[O:13])=[O:5]Tetrapropylammonium perruthenate (16 mg, 0.05 mmol) was added to a dichloromethane (5 mL) solution of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (intermediate 2, 105 mg, 0.49 mmol) and 4-methylmorpholine N-oxide (137 mg, 1.17 mmol). The solution was stirred at room temperature for 30 minutes. Water was added and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with ethyl acetate/hexanes afforded the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 9.79 (s, 1H), 5.25-5.32 (m, 1H), 4.76 (dd, J=13.0, 3.5 Hz, 1H), 4.49 (dd, J=13.0, 6.5 Hz, 1H), 2.59-2.54 (m, 2H), 1.83-1.73 (m, 4H).
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