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【结 构 式】 
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【药物名称】 【化学名称】N6-Cyclopropyl-2',3'-didehydro-2',3'-dideoxyadenosine 【CA登记号】188525-24-8 【 分 子 式 】C13H16N6O2 【 分 子 量 】288.31147 |
【开发单位】University of Georgia (Originator), Yale University (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, Reverse Transcriptase Inhibitors |
合成路线1
Treatment of 2-amino-6-chloro-9-beta-D-ribofuranosylpurine (I) with acetoxyisobutyryl bromide (II) led to a mixture of acetoxy bromo derivatives (III) and (IV) which, upon reductive treatment with activated zinc, furnished the 2',3'-dehydro compound (V). Deprotection of (V) with K2CO3 in aqueous methanol provided the free nucleoside (VI). Finally, nucleophilic displacement of the chlorine of (VI) with cyclopropylamine (VII) afforded the target compound.
| 【1】 Chu, C.K.; Ray, A.S.; Anderson, K.S.; Yang, Z.; Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent. Antimicrob Agents Chemother 2002, 46, 3, 887. |
| 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) | 55888 | (2R,3S,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C10H12ClN5O4 | 详情 | 详情 | |
| (II) | 12806 | 2-bromo-1,1-dimethyl-2-oxoethyl acetate; alpha-Acetoxy-isobutyryl bromide | 40635-67-4 | C6H9BrO3 | 详情 | 详情 |
| (III) | 55889 | (2R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-bromo-5-{[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl}tetrahydro-3-furanyl acetate | C18H21BrClN5O7 | 详情 | 详情 | |
| (IV) | 55890 | (2R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-4-bromo-2-{[(2,4,4-trimethyl-5-oxo-1,3-dioxolan-2-yl)oxy]methyl}tetrahydro-3-furanyl acetate | C18H21BrClN5O7 | 详情 | 详情 | |
| (V) | 55891 | 2-{[(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methoxy}-2,5,5-trimethyl-1,3-dioxolan-4-one | C16H18ClN5O5 | 详情 | 详情 | |
| (VI) | 55892 | [(2S,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2,5-dihydro-2-furanyl]methanol | C10H10ClN5O2 | 详情 | 详情 | |
| (VII) | 12263 | Cyclopropylamine; Cyclopropanamine | 765-30-0 | C3H7N | 详情 | 详情 |