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【结 构 式】 
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【分子编号】32131 【品名】5-(chloromethyl)-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione 【CA登记号】 |
【 分 子 式 】C10H13ClN2O6 【 分 子 量 】292.6758 【元素组成】C 41.04% H 4.48% Cl 12.11% N 9.57% O 32.8% |
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：(II)Treatment of 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil (I) with hydrogen chloride in dioxane affords the 5-chloromethyl derivative (II), which is converted to the triphenylphosphonium salt (III). The Wittig reaction of (III) by means of paraformaldehyde and n-butyllithium in DMF yields the 5-vinyl derivative (IV), and bromination of (IV) with bromine in DMF under a heated condition affords BVAU.
| 【1】 Senda, S.; Mizuno, Y.; Shibuya, S.; Ikeda, K.; Sakata, S.; Machida, H.; Hirota, K.; Yoshino, H.; Synthesis and antiherpes-viral activity of 5-C-substituted uracil nucleosides. Nucleic Acids Res Symp Ser 1980, 8, 8, S39-S42. |
| 【2】 Sakata, S.; Machida, H.; BVAU. Drugs Fut 1982, 7, 7, 458. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 32130 | 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-(hydroxymethyl)-2,4(1H,3H)-pyrimidinedione; 5-hydroxymethyl-1-beta-D-arabinofuranosyluracil | C10H14N2O7 | 详情 | 详情 | |
| (II) | 32131 | 5-(chloromethyl)-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione | C10H13ClN2O6 | 详情 | 详情 | |
| (III) | 32132 | ([1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]methyl)(triphenyl)phosphonium chloride | C28H28ClN2O6P | 详情 | 详情 | |
| (IV) | 32133 | 1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-vinyl-2,4(1H,3H)-pyrimidinedione | C11H14N2O6 | 详情 | 详情 |
Extended Information