[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][C:6]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CCN(CC)CC.N1C=CC=CC=1.CCOC(C)=O>CS(C)=O>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][C:6]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1The alcohol from Step C above (25 g, 89 mmol) was dissolved in 500 mL of anhydrous DMSO. To this solution was added Et3N (50 mL, 358 mmol). Then SO3.Pyridine (57 g, 358 mmol), was dissolved in 400 mL of DMSO, and this solution was added to the reaction vessel. The solution was then stirred at room temperature for two hours. The reaction solution was then poured over ice and the resulting mixture was warmed to room temperature and extracted with CH2Cl2. The organic layer was washed with 1M HCl, water, and brine, then the organic layer was dried over MgSO4, filtered and evaporated. The crude product was chromatographed on silica gel, eluting with 10:1 hexane:EtOAc to give the title product as a colorless oil (20 g, 81% yield).
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