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【结 构 式】 
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【分子编号】41254 【品名】(3R,4R,5S)-4-(benzoyloxy)-5-(chloromethyl)-2-methoxytetrahydro-3-furanyl benzoate 【CA登记号】 |
【 分 子 式 】C20H19ClO6 【 分 子 量 】390.81996 【元素组成】C 61.47% H 4.9% Cl 9.07% O 24.56% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of methyl D-ribofuranoside (I) with SOCl2 gives methyl 5-chloro-5-deoxy-2,3-O-sulfinyl-D-ribofuranoside (II), which is treated with ammonia to yield methyl 5-chloro-5-deoxy-D-ribofuranoside (III). The reaction of (IV) with benzoyl chloride and pyridine affords the dibenzoate (IV), which is treated with lithium azide in DMF to provide the 5'-azido derivative (V). The condensation of 3-iodo-1H-pyrazolo[3,4-d]pyrimidine-4-amine (VII) (prepared by iodination of (1H-pyrazolo[3,4-d]pyrimidine-4-amine (VI) with N-iodosuccinimide (NIS)) with the azido derivative (V) by means of BF3/Et in nitromethane gives the adduct (VIII), which is debenzoylated with sodium methoxide yielding the azido nucleoside (IX). Finally this compound is reduced with triphenylphosphine and ammonia to furnish the target 5'-amino-nucleoside.
| 【1】 Cottam, H.B.; New adenosine kinase inhibitors with oral antiinflammatory activity. Drugs Fut 1994, 19, 5, 485. |
| 【2】 Kasukhin, L.F.; Gololobov, Yu.G.; Zhmurova, I.N.; Sixty years of Staudinger reaction. Tetrahedron 1981, 37, 437-472. |
| 【3】 Browne, C.E.; Ugarkar, B.G.; Mullane, K.M.; Gruber, H.E.; Bullough, D.A.; Erion, M.D.; Castellino, A. (Sicor Inc.); Adenosine kinase inhibitors. EP 0496617; JP 1993112595; WO 9212718 . |
| 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) | 41258 | (2R,3S,4R)-2-(hydroxymethyl)-5-methoxytetrahydro-3,4-furandiol | C6H12O5 | 详情 | 详情 | |
| (II) | 41252 | (4S)-4-(chloromethyl)-6-methoxytetrahydro-2lambda(4)-furo[3,4-d][1,3,2]dioxathiol-2-one | C6H9ClO5S | 详情 | 详情 | |
| (III) | 41253 | (2S,3S,4R)-2-(chloromethyl)-5-methoxytetrahydro-3,4-furandiol | C6H11ClO4 | 详情 | 详情 | |
| (IV) | 41254 | (3R,4R,5S)-4-(benzoyloxy)-5-(chloromethyl)-2-methoxytetrahydro-3-furanyl benzoate | C20H19ClO6 | 详情 | 详情 | |
| (V) | 41255 | (3R,4R,5R)-5-(azidomethyl)-4-(benzoyloxy)-2-methoxytetrahydro-3-furanyl benzoate | C20H19N3O6 | 详情 | 详情 | |
| (VI) | 41249 | 4-amine-1H-pyrazolo[3,4-d]pyrimidine; 1H-pyrazolo[3,4-d]pyrimidin-4-ylamine; 1H-pyrazolo[3,4-d]pyrimidin-4-amine | 2380-63-4 | C5H5N5 | 详情 | 详情 |
| (VII) | 41250 | 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine | C5H4IN5 | 详情 | 详情 | |
| (VIII) | 41256 | (2R,3R,4R,5R)-2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-(azidomethyl)-4-(benzoyloxy)tetrahydro-3-furanyl benzoate | C24H19IN8O5 | 详情 | 详情 | |
| (IX) | 41257 | (2R,3R,4S,5R)-2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-5-(azidomethyl)tetrahydro-3,4-furandiol | C10H11IN8O3 | 详情 | 详情 |