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【结 构 式】 
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【分子编号】26427 【品名】[(2S,4S)-4-(6-amino-9H-purin-9-yl)tetrahydro-2-furanyl]methyl 4-nitrobenzoate 【CA登记号】 |
【 分 子 式 】C17H16N6O5 【 分 子 量 】384.35148 【元素组成】C 53.13% H 4.2% N 21.87% O 20.81% |
合成路线1
该中间体在本合成路线中的序号：(IX)The reaction of silylated (S)-glycidol (I) with the vinyl copper compound (II) in ethyl ether gives the monosilylated unsaturated diol (III), which is desilylated with Bu4NF in THF yielding the diol (IV). The cyclization of (IV) by means of I2 and NaHCO3 in acetonitrile affords a mixture of the cis and trans diastereomers from which the trans isomer (V) was isolated. The acylation of (V) with potassium 4-nitrobenzoate (VI) in DMSO/18-crown-6 yields the 4-nitrobenzoyl ester (VII), which is condensed with adenine (VIII) by means of DEAD and triphenylphosphine in DMF providing the 4-nitrobenzoyl percursor (IX). Finally, (IX) is debenzoylated with NaOMe in methanol.
| 【1】 Diaz, Y.; et al.; Synthesis of purine and pyrimidine isodideoxynucleosides from (S)-glycydol using iodoetherification as key step. Synthesis of (S,S)-iso-ddA. J Org Chem 1999, 64, 17, 6508. |
| 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) | 26421 | tert-butyl[(2R)oxiranylmethoxy]diphenylsilane; tert-butyl(diphenyl)silyl (2R)oxiranylmethyl ether | C19H24O2Si | 详情 | 详情 | |
| (III) | 26422 | (2R)-1-[[tert-butyl(diphenyl)silyl]oxy]-4-penten-2-ol | C21H28O2Si | 详情 | 详情 | |
| (IV) | 26423 | (2R)-4-pentene-1,2-diol | C5H10O2 | 详情 | 详情 | |
| (V) | 26424 | (3R,5S)-5-(iodomethyl)tetrahydro-3-furanol | C5H9IO2 | 详情 | 详情 | |
| (VI) | 26425 | potassium 4-nitrobenzoate | 15922-01-7 | C7H4KNO4 | 详情 | 详情 |
| (VII) | 26426 | [(2S,4R)-4-hydroxytetrahydro-2-furanyl]methyl 4-nitrobenzoate | C12H13NO6 | 详情 | 详情 | |
| (VIII) | 10343 | 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine | 73-24-5 | C5H5N5 | 详情 | 详情 |
| (IX) | 26427 | [(2S,4S)-4-(6-amino-9H-purin-9-yl)tetrahydro-2-furanyl]methyl 4-nitrobenzoate | C17H16N6O5 | 详情 | 详情 |