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【结 构 式】 
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【分子编号】39188 【品名】(E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]-2-propenoic acid 【CA登记号】 |
【 分 子 式 】C12H14N2O7 【 分 子 量 】298.25244 【元素组成】C 48.33% H 4.73% N 9.39% O 37.55% |
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：(IV)5-Chloromercuri-2'-deoxyuridine (II) is prepared from 2'-deoxyuridine (I) by reaction with mercuriacetate and natrium chloride (1). Condensation of (II) with ethylacrylate (A) and lithium palladium chloride gives (E)-5-(2-carbethoxyvinyl)-2'-deoxyuridine (III), which is readily hydrozyled to (E)-5-(2-carboxyvinyl)-2'-deoxyuridine (IV) under basic conditions (0.5M NaOH). The final step involves the reaction of (IV) with N-bromosuccinimide to produce (E)-5-(2-bromovinyl)-2'-deoxyuridine.
| 【1】 Bergstrom, D.E.; Ruth, J.L.; Preparation of C-5 mercurated pyrimidine nucleosides. J Carbohydates Nucleosides Nucleotides 1977, 4, 5, 4415. |
| 【2】 De Clercq, E.; Bromovinyldeoxyuridine. Drugs Fut 1980, 5, 7, 334. |
| 【3】 Jones, A.S.; et al.; The synthesis of the potent antiherpes virus agent, E-5(2-bromovinyl)-2'-deoxyuridine and related compounds. Tetrahedron Lett 1979, 45, 4415-8. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (I) | 11875 | 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; 2'-Deoxyuridine | 951-78-0 | C9H12N2O5 | 详情 | 详情 |
| (II) | 39186 | chloro[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]mercury | C9H11ClHgN2O5 | 详情 | 详情 | |
| (III) | 39187 | ethyl (E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]-2-propenoate | C14H18N2O7 | 详情 | 详情 | |
| (IV) | 39188 | (E)-3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]-2-propenoic acid | C12H14N2O7 | 详情 | 详情 |
Extended Information