[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@@H:12]2[O:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O>C1COCC1.[Cu](Cl)(Cl)(Cl)Cl.[Li]>[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@H:12]([OH:14])[CH2:13][CH2:3][CH2:2][C@@H:1]([CH3:15])[CH2:6][CH3:5])(=[O:9])=[O:8])=[CH:3][CH:2]=1Separately, 0.42 g of lithium copper tetrachloride was dissolved in 80 ml of THF in a flask, and the solution was cooled to -50° C. The above prepared Grignard reagent was added dropwise to the solution at that temperature, followed by stirring for 15 minutes. After cooling the reaction mixture to -55° C., a mixture of 2.0 g of (R)-glycidyl p-toluenesulfonate and 20 ml of THF was added thereto dropwise to conduct reaction at that temperature for 1.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated to obtain 2.85 g (25.64%) of the titled compound.
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