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【结 构 式】 
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【分子编号】45367 【品名】6-oxabicyclo[3.1.0]hex-2-ene 【CA登记号】 |
【 分 子 式 】C5H6O 【 分 子 量 】82.10204 【元素组成】C 73.15% H 7.37% O 19.49% |
合成路线1
该中间体在本合成路线中的序号：(II)The condensation of 6-chloropurine-2-amine (I) with epoxide (II) by means of Pd(PPh3)4 in DMSO gives the cyclopentenol derivative (III), which is treated with dimethyl dicarbonate and DMAP in dichloromethane to yield the carbonate (IV). The condensation of (IV) with ethyl 2-nitroacetate (V) by means of Pd in THF affords the adduct (VI), which is decarboxylated by means of NaCl in DMSO/water at 150 C to provide the nitromethylcyclopentene derivative (VII). The reaction of (VII) with tBuOK, O3 and NaBH4 in methanol gives the corresponding hydroxymethyl derivative (VIII), which is finally hydrolyzed with NaOH in refluxing water to afford the target guanine as a racemic compound. Alternatively, the nitromethyl-cyclopentene derivative (VII) can also be obtained by condensation of carbonate (IV) with 2-(trimethylsilyl)ethyl 2-nitroacetate (IX) by means of Pd in THF to give the adduct (X), which is decarboxylated by means of CsF in hot acetonitrile, affording (VII).
| 【1】 Peel, M.R.; et al.; A short, enantioselective synthesis of the carbocyclic nucleoside carbovir. J Org Chem 1991, 56, 16, 4990. |
| 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) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (II) | 45367 | 6-oxabicyclo[3.1.0]hex-2-ene | C5H6O | 详情 | 详情 | |
| (III) | 45368 | (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-ol | C10H10ClN5O | 详情 | 详情 | |
| (IV) | 45369 | (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl methyl carbonate | C12H12ClN5O3 | 详情 | 详情 | |
| (V) | 15050 | ethyl 2-nitroacetate; Acetic acid, nitro-, ethyl ester | 626-35-7 | C4H7NO4 | 详情 | 详情 |
| (VI) | 45370 | ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate | C14H15ClN6O4 | 详情 | 详情 | |
| (VII) | 45371 | 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-ylamine; 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-amine | C11H11ClN6O2 | 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 | |
| (IX) | 45372 | 2-(trimethylsilyl)ethyl 2-nitroacetate | C7H15NO4Si | 详情 | 详情 | |
| (X) | 45373 | 2-(trimethylsilyl)ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate | C17H23ClN6O4Si | 详情 | 详情 |