[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C@H:11](OS(C(F)(F)F)(=O)=O)[C@H:10]([N:21]2[C:25]3[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=3[S:23][C:22]2=[O:32])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2].[CH3:33][S-:34].[Na+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:4][CH:5]([C@@H:8]1[CH2:12][C@@H:11]([S:34][CH3:33])[C@H:10]([N:21]2[C:25]3[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=3[S:23][C:22]2=[O:32])[O:9]1)[CH2:6][CH3:7])(=[O:3])[CH3:2]To a stirred solution of 1-[(2S,4S,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-(trifluoromethylsulfonyloxy)tetrahydrofuran-2-yl]propyl acetate (compound 22d, 420 mg, 0.83 mmol) in DMF (7 mL) was added sodium thiomethoxide (84 mg, 1.2 mmol). After being stirred at room temperature for 2 hours, the resulting solution was diluted with EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo to afford crude product of 1-[(2S,4R,5R)-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)-4-methylsulfanyl-tetrahydrofuran-2-yl]propyl acetate (compound 22e), which was used in next step without further purification. MS obsd. (ESI−) [(M−H)−]: 399.
Wird geladen…