C(N(CC)CC)C.[OH:8][C@:9]1([C:21]([O:23][CH3:24])=[O:22])[CH2:19][C@@H:18]([OH:20])[C@@H:12]2[O:13][C:14]([CH3:17])([CH3:16])[O:15][C@@H:11]2[CH2:10]1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[OH:8][C@:9]1([C:21]([O:23][CH3:24])=[O:22])[CH2:19][C@@H:18]([O:20][S:26]([CH3:25])(=[O:28])=[O:27])[C@@H:12]2[O:13][C:14]([CH3:16])([CH3:17])[O:15][C@@H:11]2[CH2:10]1Triethylamine (5.0 mL, 35.9 mmol) was added dropwise to a 0° C. solution of Example 13B (4.4 g, 17.9 mmol) and methanesulfonyl chloride (1.38 mL, 17.9 mmol) in dichloromethane (60 mL). After stirring overnight, the reaction mixture was washed with saturated sodium bicarbonate, brine, dried (MgSO4), filtered and concentrated to afford the crude desired product.
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