Benzoyl chloride → N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5-fluorocytidine

反応式

[F:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]([NH:17][C:3]1[C:2]([F:1])=[CH:15][N:6]([C@@H:7]2[O:14][C@H:12]([CH3:13])[C@@H:10]([O:11][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:8]2[O:9][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5](=[O:16])[N:4]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

実験手順

5'-Deoxy-5-fluorocytidine (245 mg), benzoyl chloride (400 μl) and 4-dimethylaminopyridine (122 mg) were dissolved in dry pyridine (5 ml). After stirring for 3 hours at room temperature pyridine was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from methanol to give N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5-fluorocytidine (280 mg), mp 158°~160° C.; MS 558 (MH+).