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【结 构 式】 
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【分子编号】69283 【品名】(1R,2R)-dimethyl 4-oxocyclopentane-1,2-dicarboxylate 【CA登记号】 |
【 分 子 式 】C9H12O5 【 分 子 量 】200.19128 【元素组成】C 54% H 6.04% O 39.96% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXI)Enzymatic resolution of trans-dimethyl 4-oxocyclopentane-1,2- dicarboxylate (rac-[XXI]) with pig liver esterase A (PLE-A) provides the desired (1R,2R)-enantiomer (XXI) (by selective hydrolysis of the [1S,2S]-enantiomer) . Reduction of ketone (XXI) with NaBH4 affords the meso-cyclopentanol derivative (XXII), which is finally treated with NaOH in MeOH and then with acetic anhydride in pyridine to provide the bicyclic lactone (VI) .
| 【1】 Rosenquist, A., Kvarntröm, I., Svensson, S.C.T., Classon, B., Samuelsson, B. Synthesis of enantiomerically pure trans-3,4-substituted cyclopentanols by enzymatic resolution. Acta Chem Scand 1992, 46: 1127-9. |
| 【2】 Johansson, P.O., Bäck, M., Kvarnström, I. et al. Potent inhibitors of the hepatitis C virus NS3 protease: Use of a novel P2 cyclopentane-derived template. Bioorg Med Chem 2006, 14(15): 5136-51. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (rac-(XXI) | 69282 | racemic dimethyl 4-oxocyclopentane-1,2-dicarboxylate | C9H12O5 | 详情 | 详情 | |
| (VI) | 69267 | (1S,4S,5S)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid | C7H8O4 | 详情 | 详情 | |
| (XXI) | 69283 | (1R,2R)-dimethyl 4-oxocyclopentane-1,2-dicarboxylate | C9H12O5 | 详情 | 详情 | |
| (XXII) | 69284 | (1R,2R)-dimethyl 4-hydroxycyclopentane-1,2-dicarboxylate | C9H14O5 | 详情 | 详情 |
Extended Information