[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][OH:19])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH2:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I:35]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([CH2:18][O:19][C:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:28][I:35])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.
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