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【结 构 式】 
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【分子编号】38541 【品名】5-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-4-pentynyl tetrahydro-2H-pyran-2-yl ether; 2-[(5-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-4-pentynyl)oxy]tetrahydro-2H-pyran 【CA登记号】 |
【 分 子 式 】C21H27FO4 【 分 子 量 】362.4413832 【元素组成】C 69.59% H 7.51% F 5.24% O 17.66% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of oxirane (I) with vinylmagnesium bromide in THF gives 1-(4-fluorophenoxy)-4-penten-2(S)-ol (II), which is treated with ethyl vinyl ether and mercuric trifluoroacetate to yield the vinyl ether (III). The cyclization of (III) by means of Grubb's catalyst in refluxing benzene affords the dihydrofuran (IV), which is treated with benzenesulfinic acid in dichloromethane to give the sulfone (V). The reaction of (V) with the acetylenic tetrahydropyranyl ether (VI) by means of isopropylmagnesium bromide in THF yields the expected addition product (VII), which is treated with TsOH to eliminate the tetrahydropyranyl group and provide the alcohol (VIII). The condensation of (VIII) with N,O-bis (phenoxycarbonyl)hydroxylamine (IX) by means of PPh3 and DEAD in THF affords the protected carbamate derivative (X), which is finally treated with ammonia in methanol.
| 【1】 Gurjar, M.K.; et al.; A versatile approach to anti-asthmatic compound CMI-977 and its six-membered analogue. Synthesis 2000, 4, 557. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16524 | bromo(vinyl)magnesium | 1826-67-1 | C2H3BrMg | 详情 | 详情 | |
| 18762 | 1-Ethoxyethylene; Ethyl vinyl ether；Ethoxyethene | 109-92-2 | C4H8O | 详情 | 详情 | |
| 40726 | dioxo(phenyl)-lambda(6)-sulfane | C6H6O2S | 详情 | 详情 | ||
| (I) | 32986 | 4-fluorophenyl (2S)oxiranylmethyl ether; (2S)-2-[(4-fluorophenoxy)methyl]oxirane | 108648-25-5 | C9H9FO2 | 详情 | 详情 |
| (II) | 38536 | (2S)-1-(4-fluorophenoxy)-4-penten-2-ol | C11H13FO2 | 详情 | 详情 | |
| (III) | 38537 | (1S)-1-[(4-fluorophenoxy)methyl]-3-butenyl vinyl ether; 1-fluoro-4-[[(2S)-2-(vinyloxy)-4-pentenyl]oxy]benzene | C13H15FO2 | 详情 | 详情 | |
| (IV) | 38538 | (2S)-2-[(4-fluorophenoxy)methyl]-2,3-dihydrofuran; (2S)-2,3-dihydro-2-furanylmethyl 4-fluorophenyl ether | C11H11FO2 | 详情 | 详情 | |
| (V) | 38539 | (2S,5R)-2-[(4-fluorophenoxy)methyl]-5-(phenylsulfonyl)tetrahydrofuran; (2R,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl phenyl sulfone | C17H17FO4S | 详情 | 详情 | |
| (VI) | 38540 | 2-(4-pentynyloxy)tetrahydro-2H-pyran; 4-pentynyl tetrahydro-2H-pyran-2-yl ether | 62992-46-5 | C10H16O2 | 详情 | 详情 |
| (VII) | 38541 | 5-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-4-pentynyl tetrahydro-2H-pyran-2-yl ether; 2-[(5-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-4-pentynyl)oxy]tetrahydro-2H-pyran | C21H27FO4 | 详情 | 详情 | |
| (VIII) | 19645 | 4-[(2S,5S)-5-[(4-fluorophenoxy)methyl]tetrahydro-2-furanyl]-3-butyn-1-ol | C15H17FO3 | 详情 | 详情 | |
| (IX) | 19646 | 1-[([[(phenoxycarbonyl)oxy]amino]carbonyl)oxy]benzene | C14H11NO5 | 详情 | 详情 | |
| (X) | 19647 | (2S,5S)-2-[(4-fluorophenoxy)methyl]-5-(4-[(phenoxycarbonyl)[(phenoxycarbonyl)oxy]amino]-1-butynyl)tetrahydrofuran | C29H26FNO7 | 详情 | 详情 |