[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:21].[Na+]>C(OCC)(=O)C.O.[Ru](=O)(=O)(=O)=O>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:11](=[O:21])[CH2:12]1)(=[O:3])[CH3:2]The product from Step B (0.275 g, 1.01 mmol) was dissolved in ethyl acetate (5 mL). A solution of sodium periodate in water (0.5 g in 5 mL) and ruthenium tetroxide (13 mg, 0.10 mmol) was added, and the heterogeneous reaction stirred vigorously overnight at room temperature. An additional portion of sodium periodate in water was added (0.5 g in 5 mL) and the reaction stirred overnight. The reaction was quenched with 10% sodium thiosulfate, and filtered through celite. The phases were separated, and the organic phase dried over magnesium sulfate. Filtration and evaporation gave the title compound.
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