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【结 构 式】 
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【分子编号】45366 【品名】[(1S,4R)-4-(acetamido)-2-cyclopenten-1-yl]methyl acetate 【CA登记号】 |
【 分 子 式 】C10H15NO3 【 分 子 量 】197.23404 【元素组成】C 60.9% H 7.67% N 7.1% O 24.34% |
合成路线1
该中间体在本合成路线中的序号：(I)The hydrolysis of the diacetyl derivative (I) with Ba(OH)2 in refluxing water gives the amino alcohol (II), which is condensed with 4,6-dichloro-2-aminopyrimidine (III) by means of TEA in refluxing tert-butanol to yield the adduct (IV). The condensation of (IV) with the diazonium salt (V) affords the azo compound (VI), which is reduced with Zn/HOAc to provide the diamine (VII). The cyclization of (VII) with triethyl orthoformate gives the 6-chloropurine derivative (VIII), which is finally treated with NaOH in refluxing water to afford the target guanine derivative as a racemic compound.
| 【1】 Vince, R.; Hua, M.; Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides. J Med Chem 1990, 33, 1, 17-21. |
| 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) | 45366 | [(1S,4R)-4-(acetamido)-2-cyclopenten-1-yl]methyl acetate | C10H15NO3 | 详情 | 详情 | |
| (II) | 17647 | [(1S,4R)-4-amino-2-cyclopenten-1-yl]methanol | C6H11NO | 详情 | 详情 | |
| (III) | 14404 | 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine | 56-05-3 | C4H3Cl2N3 | 详情 | 详情 |
| (IV) | 17657 | [(1S,4R)-4-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol | C10H13ClN4O | 详情 | 详情 | |
| (V) | 10197 | 4-Chlorobenzenediazonium chloride | C6H4Cl2N2 | 详情 | 详情 | |
| (VI) | 17659 | [(1S,4R)-4-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-cyclopenten-1-yl]methanol | C16H16Cl2N6O | 详情 | 详情 | |
| (VII) | 17660 | [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol | C10H14ClN5O | 详情 | 详情 | |
| (VIII) | 17650 | [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol | C11H12ClN5O | 详情 | 详情 |