[H-].[Na+].Cl[CH2:4]/[CH:5]=[C:6](/[CH3:13])\[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11].[CH2:14]([O:16][CH2:17][PH:18]([CH2:20][P:21](=[O:28])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])=[O:19])[CH3:15].[I-].[CH3:30][CH2:31]OCC>CN(C=O)C>[CH2:14]([O:16][CH2:17][PH:18]([CH:20]([P:21](=[O:28])([O:22][CH2:23][CH3:24])[O:25][CH2:26][CH3:27])[CH2:30][CH2:31][CH2:4]/[CH:5]=[C:6](/[CH3:13])\[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])=[O:19])[CH3:15]To a stirred mixture of 123 mg (5.13 mmol) of sodium hydride in 10 mL of DMF at 0° C. under argon was added 1.32 g (5.13 mmol) of Example 1, Part A [(ethoxymethylphosphinyl)methyl]phosphonic acid, diethyl ester in 5 mL of DMF dropwise over 20 minutes. The mixture was stirred for 0.5 hours and was treated with 1.00 g (3.42 mmol) of Part A iodide in 3 mL of DMF. The reaction was stirred at 0° C. for 1 hour then at room temperature for 48 hours, at which time the reaction was diluted with ether and quenched with saturated NH4Cl. The organic layer was washed with water, brine, dried (MgSO4) and evaporated to provide 1.10 g of a pale yellow oil. Flash chromatography was performed on 100 g of silica gel eluted with 49.5:49.5:1 acetone/ethyl acetate/methanol (1 liter) followed by 45:45:10 acetone/ethyl acetate/methanol. Pure product fractions were combined and evaporated to provide 600 mg (43%) of title ester as a pale yellow oil, a mixture of diastereomers.
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