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【结 构 式】 
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【分子编号】56025 【品名】1-[(2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(tetrahydro-2H-pyran-2-yloxy)propyl]-2,4-dinitro-1H-imidazole; tert-butyl(dimethyl)silyl (2S)-3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propyl ether 【CA登记号】 |
【 分 子 式 】C17H30N4O7Si 【 分 子 量 】430.53346 【元素组成】C 47.43% H 7.02% N 13.01% O 26.01% Si 6.52% |
合成路线1
该中间体在本合成路线中的序号：(IV)Condensation of 2,4-dinitroimidazole (I) with the silyl-protected (S)-glycidol (II) gave the N-substituted imidazole (III). The free hydroxyl group of (III) was then protected as the tetrahydropyranyl ether (IV) by treatment with dihydropyran and pyridinium tosylate. Desilylation of (IV) by means of tetrabutylammonium fluoride proceeded with concomitant nitro group displacement to afford the pyranoimidazole derivative (V). The tetrahydropyranyl group of (V) was then removed by acidic hydrolysis to provide alcohol (VI). Finally, condensation of (VI) with 4-(trifluoromethoxy)benzyl bromide (VII) under Williamson's ether synthesis conditions provided the title compound.
| 【1】 Baker, W.R.; Shaopei, C.; Keeler, E.L. (PathoGenesis Corp.); Nitroimidazole antibacterial cpds. and methods of use thereof. EP 0866793; JP 1999508270; WO 9701562 . |
| 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) | 56023 | 2,4-dinitro-1H-imidazole | 5213-49-0 | C3H2N4O4 | 详情 | 详情 |
| (II) | 42416 | tert-butyl(dimethyl)[(2S)oxiranylmethoxy]silane; tert-butyl(dimethyl)silyl (2S)oxiranylmethyl ether | 123237-62-7 | C9H20O2Si | 详情 | 详情 |
| (III) | 56024 | (2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-3-(2,4-dinitro-1H-imidazol-1-yl)-2-propanol | C12H22N4O6Si | 详情 | 详情 | |
| (IV) | 56025 | 1-[(2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(tetrahydro-2H-pyran-2-yloxy)propyl]-2,4-dinitro-1H-imidazole; tert-butyl(dimethyl)silyl (2S)-3-(2,4-dinitro-1H-imidazol-1-yl)-2-(tetrahydro-2H-pyran-2-yloxy)propyl ether | C17H30N4O7Si | 详情 | 详情 | |
| (V) | 56026 | (6S)-2-nitro-6-(tetrahydro-2H-pyran-2-yloxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl tetrahydro-2H-pyran-2-yl ether | C11H15N3O5 | 详情 | 详情 | |
| (VI) | 56027 | (6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol | C6H7N3O4 | 详情 | 详情 | |
| (VII) | 20308 | 4-(bromomethyl)phenyl trifluoromethyl ether; 1-(bromomethyl)-4-(trifluoromethoxy)benzene | 50824-05-0 | C8H6BrF3O | 详情 | 详情 |