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【结 构 式】 
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【分子编号】62376 【品名】(3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 【CA登记号】 |
【 分 子 式 】C13H14ClN5O5 【 分 子 量 】355.73756 【元素组成】C 43.89% H 3.97% Cl 9.97% N 19.69% O 22.49% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Acetonide (VII) was prepared by treatment of 2-chloroadenosine (VI) with 2,2-dimethoxypropane and camphorsulfonic acid. Subsequent oxidation of (VII) with KMnO4 under basic conditions produced the carboxylic acid (VIII). After activation of (VIII) as the corresponding acid chloride (IX), reaction with ethylamine afforded amide (X). Condensation of amine (V) with the chloroadenosine derivative (X) at 130 C furnished the diaminopurine adduct (XI). Finally, simultaneous cleavage of the tert-butyl ester and acetonide groups of (XI) upon acidic treatment provided the title compound
| 【1】 Hutchison, A.J.; Williams, M.; de Jesus, R.; Yokoyama, R.; Oei, H.H.; Ghai, G.R.; Webb, R.L.; Zoganas, H.C.; Stone, G.A.; Jarvis, M.F.; 2-(Arylalkylamino)adenosin-5'-uronamides: A new class of highly selective adenosine A2 receptor ligands. J Med Chem 1990, 33, 7, 1919. |
| 【2】 Hutchison, A.J. (Novartis AG); Certain adenosine 5'-carboxamide derivs.. AU 8811233; EP 0277917; JP 1988201196 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 62373 | tert-butyl 3-[4-(2-aminoethyl)phenyl]propanoate | C15H23NO2 | 详情 | 详情 | |
| (VI) | 62374 | (2R,3R,4S,5R)-2-(6-amino-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol | C10H12ClN5O4 | 详情 | 详情 | |
| (VII) | 62375 | [(3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol | C13H16ClN5O4 | 详情 | 详情 | |
| (VIII) | 62376 | (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid | C13H14ClN5O5 | 详情 | 详情 | |
| (IX) | 62377 | (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl chloride | C13H13Cl2N5O4 | 详情 | 详情 | |
| (X) | 62378 | (3aR,4S,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-N-ethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide | C15H19ClN6O4 | 详情 | 详情 | |
| (XI) | 62379 | tert-butyl 3-(4-{2-[(9-{(3aR,4R,6S,6aR)-6-[(ethylamino)carbonyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-amino-9H-purin-2-yl)amino]ethyl}phenyl)propanoate | C30H41N7O6 | 详情 | 详情 |