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【结 构 式】 
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【药物名称】Tetrahydrouridine, NSC-112907, THU 【化学名称】1(-beta-D-Ribofuranosyl)-4-hydroxytetrahydropyrimidin-2(1H)-one 【CA登记号】18771-50-1 【 分 子 式 】C9H16N2O6 【 分 子 量 】248.23767 |
【开发单位】 【药理作用】 |
合成路线1
Compound can be prepared in three different ways: 1) The reduction of cytidine (I) with H2 over Rh/Al2O3 in water in a Parr apparatus at 2.8 bar gives 3,4,5,6-tetrahydrocytidine (II), which is then hydrolyzed with water at pH 5.5. 2) The reduction of uridine (III) with H2 over Rh/Al2O3 as before gives 5,6-dihydrouridine (IV), which is then reduced again with NaBH4 in water or with H2 over Rh/Al2O3 in water containing ammonia. 3) The reduction of (III) can also be performed in a single step with H2 over Rh/Al2O3 in water containing NH3, in a Parr apparatus at 2.94 bar.
| 【1】 Woodman, R.J.; Tetrahydrouridine. Drugs Fut 1979, 4, 4, 283. |
| 【2】 Hanze, A.R.; Nucleic acids. IV. The catalytic reduction of pyrimidine nucleosides (human liver deaminase inhibitors). J Am Chem Soc 1967, 89, 25, 6720-25. |
| 【3】 Hanze, A.R.; Camiener, G.W.; US 3462416 . |
| 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) | 27920 | Cytidine; 4-amino-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone | 65-46-3 | C9H13N3O5 | 详情 | 详情 |
| (II) | 39509 | 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]tetrahydro-2(1H)-pyrimidinone | C9H17N3O5 | 详情 | 详情 | |
| (III) | 11996 | 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione; Uridine | 58-96-8 | C9H12N2O6 | 详情 | 详情 |
| (IV) | 39510 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]dihydro-2,4(1H,3H)-pyrimidinedione | C9H14N2O6 | 详情 | 详情 |