[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[CH2:19][O:20][C:21](=[O:31])NC(=O)C1C=CC=CC=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+:33]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:21]([O:20][CH2:19][C@@H:17]1[C@@H:16]([CH2:15][O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:18][C:1](=[O:4])[NH:33]1)(=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Potassium carbonate (4.04 g, 29.2 mmol) and tetrabutylammonium iodide (800 mg, 2.2 mmol) were added to an acetonitrile solution (100 mL) containing 5.8 g of benzoylcarbamate (2), and the mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride aqueous solution was added to the reaction solution to quench the reaction. After ether extraction, the organic layer was dried over magnesium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (ether/hexane=2/1) to obtain 4.87 g of a mixture of the title compounds (3 steps, 98%).
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