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【结 构 式】 
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【分子编号】17463 【品名】(1R,4S,6R)-4-[(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-3,7-dioxabicyclo[4.1.0]heptan-2-one 【CA登记号】 |
【 分 子 式 】C25H20FNO3 【 分 子 量 】401.4371432 【元素组成】C 74.8% H 5.02% F 4.73% N 3.49% O 11.96% |
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：(XLV)Elimination of thiophenol from (XLIII) by means of CaCO3 in refluxing toluene gives the unsaturated lactone (XLIV) with the (E)-vinylene bond. The alpha,beta-epoxidation of the unsaturated lactone (XLIV) with H2O2 and NaOH in methanol/dichloromethane affords the monoepoxy lactone (XLV) regioselectively, which is finally submitted to a regioselective ring opening with diphenyl diselenide and NaBH4 in THF.
| 【1】 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; NK-104. Drugs Fut 1998, 23, 8, 847-859. |
| 【2】 Kamikubo, T.; Takano, S.; Sugihara, T.; Suzuki, M.; Ogasawara, K.; Enantioconvergent synthesis of a promising HMG-CoA reductase inhibitor NK-104 from both enantiomers of epichlorohydrin. Tetrahedron Asymmetry 1993, 4, 2, 201-4. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XLIII) | 17457 | (6S)-6-[2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-(phenylsulfinyl)ethyl]-5,6-dihydro-2H-pyran-2-one | C31H26FNO3S | 详情 | 详情 | |
| (XLIV) | 17462 | (6S)-6-[(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-5,6-dihydro-2H-pyran-2-one | C25H20FNO2 | 详情 | 详情 | |
| (XLV) | 17463 | (1R,4S,6R)-4-[(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-3,7-dioxabicyclo[4.1.0]heptan-2-one | C25H20FNO3 | 详情 | 详情 | |
| (XLVI) | 64696 | (4R,6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl}-4-hydroxytetrahydro-2H-pyran-2-one | C25H22FNO3 | 详情 | 详情 |
Extended Information