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【结 构 式】 
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【药物名称】 【化学名称】N6-Hydroxycytidine 【CA登记号】3258-02-4, 85373-26-8 (deleted CAS) 【 分 子 式 】C9H13N3O6 【 分 子 量 】259.22046 |
【开发单位】Pharmasset (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
Treatment of 2',3'-O-isopropylidene-5'-O-trityluridine (I) with 2,4,6-triisopropylbenzenesulfonyl chloride (II) in the presence of DMAP affords the sulfonic ester derivative (III). Subsequent displacement of sulfonate (III) with hydroxylamine leads to the protected N-hydroxycytidine (IV). The protecting groups of (IV) are finally removed with aqueous trifluoroacetic acid to furnish the title compound.
| 【1】 Watanabe, K.A.; Stuyver, L. (Pharmasset, Inc.); Modified nucleosides for treatment of viral infections and abnormal cellular proliferation. WO 0232920 . |
| 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) | 64247 | 1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2,4(1H,3H)-pyrimidinedione | C31H30N2O6 | 详情 | 详情 | |
| (II) | 14545 | 2,4,6-triisopropylbenzenesulfonyl chloride | 6553-96-4 | C15H23ClO2S | 详情 | 详情 |
| (III) | 64248 | 1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2-oxo-1,2-dihydro-4-pyrimidinyl 2,4,6-triisopropylbenzenesulfonate | C46H52N2O8S | 详情 | 详情 | |
| (IV) | 64249 | 1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-4-(hydroxyamino)-2(1H)-pyrimidinone | C31H31N3O6 | 详情 | 详情 |
Extended Information