[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16]C(C)(C)C(C)(C)[O:13]2)=[CH:8][C:7]=1[O:21][CH3:22].I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([B:12]([OH:13])[OH:16])=[CH:8][C:7]=1[O:21][CH3:22]
To a solution of the compound (179.0 mg, 0.50 mmol) prepared in Example 9 in 10 mL acetone were added sodium periodate (318.0 mg, 1.49 mmol), ammonium acetate (84.0 mg, 1.09 mmol), and water (10 mL). The suspension was allowed to stir at room temperature for 18 hours. The acetone was removed under reduced pressure and the resulting aqueous layer was acidified with concentrated hydrochloric acid to pH 3. The resulting solid was collected and washed several times with water then dried under vacuum to obtain the title compound (106 mg) having the following physical data.
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