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【结 构 式】 
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【分子编号】31164 【品名】3-benzoyl-1-[(2R,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C24H21F3N2O6 【 分 子 量 】490.4358296 【元素组成】C 58.78% H 4.32% F 11.62% N 5.71% O 19.57% |
合成路线1
该中间体在本合成路线中的序号：(VIII)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 |