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【结 构 式】

【分子编号】31163

【品名】3-benzoyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【 分 子 式 】C17H15F3N2O6

【 分 子 量 】400.3111896

【元素组成】C 51.01% H 3.78% F 14.24% N 7% O 23.98%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

The benzoylation of 2'-deoxy-5-(trifluoromethyl)uridine (VI) with benzoyl chloride by means of triethylamine in dimethylacetamide gives 3-benzoyl-2'-deoxy-5-(trifluoromethyl)uridine (VII), which is benzylated with benzyl bromide and silver oxide in refluxing 2-butanone to afford 3-benzoyl-3'-O-benzyl-2'-deoxy-5-(trifluoromethyl)uridine (VIII). Finally, this compound is debenzoylated with 30% aqueous ammonia at room temperature. The deprotection of 2'-deoxy-3'-O-(thiobenzoyl)-5-(trifluoromethyl)-5'-O-trityluridine (XIII) with 0.1N HCl gives 2'-deoxy-3'-O-(thiobenzoyl)-5-(trifluoromethyl)uridine (XIV), which is submitted to desulfurization with Raney-Ni in THF.

1 Noguchi, K.; Yasumoto, M.; Kobayashi, K. (Taiho Pharmaceutical Co., Ltd.); Method for the preparation of 5-trifluromethyl-2'-deoxy-beta-uridines. JP 1988145296 .
2 Yamashita, J.-I.; Matsumoto, H.; Kobayashi, K.; Noguchi, K.; Yasumoto, M.; Ueda, T.; Studies on antitumor agents. IX. Synthesis of 3'-O-benzyl-2'-deoxy-5-trifluromethyluridine. Chem Pharm Bull 1989, 37, 9, 2287-92.
3 Hoshi, A.; Prous, J.; Castaner, J.; FTC-092. Drugs Fut 1990, 15, 8, 790.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10463 Benzoyl chloride 98-88-4 C7H5ClO 详情 详情
12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(VI) 31162 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione 70-00-8 C10H11F3N2O5 详情 详情
(VII) 31163 3-benzoyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione C17H15F3N2O6 详情 详情
(VIII) 31164 3-benzoyl-1-[(2R,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione C24H21F3N2O6 详情 详情
(XIII) 31165 O-[(2R,3S,5R)-5-[2,4-dioxo-5-(trifluoromethyl)-3,4-dihydro-1(2H)-pyrimidinyl]-2-[(trityloxy)methyl]tetrahydro-3-furanyl] benzenecarbothioate C36H29F3N2O5S 详情 详情
(XIV) 31166 O-[(2R,3S,5R)-5-[2,4-dioxo-5-(trifluoromethyl)-3,4-dihydro-1(2H)-pyrimidinyl]-2-(hydroxymethyl)tetrahydro-3-furanyl] benzenecarbothioate C17H15F3N2O5S 详情 详情
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