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【结 构 式】 
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【分子编号】54255 【品名】(1R,2S)-3-(acetyloxy)-2-[(acetyloxy)methoxy]-1-[(acetyloxy)methyl]propyl acetate 【CA登记号】n/a |
【 分 子 式 】C13H20O9 【 分 子 量 】320.2964 【元素组成】C 48.75% H 6.29% O 44.96% |
合成路线1
该中间体在本合成路线中的序号：(IV)The acetylation of meso-erythritol (I) with 3 equivalents of Ac2O in pyridine gives 1,3,4-triacetoxy-meso-erythritol (II) with some tetraacetoxy derivative that is separated by chromatography. The reaction of (II) with P2O5 and dimethoxyethane yields 1,3,4-triacetoxy-2-(methoxymethoxy)butane (III), which is treated with Ac2O and BF3/Et2O to afford 1,3,4-triacetoxy-2-(acetoxymethoxy)butane (IV). The condensation of (IV) with 2-nitroimidazole (V) by means of Ts-OH at 130 C or by means of hot N,N-bis(trimethylsilyl)acetamide (BSA) provides the precursor (VI), which is finally deacetylated by means of EtONa in ethanol or TEA in aqueous methanol to furnish the target trihydroxy derivative.
| 【1】 Suzuki, T.; Sakaguchi, M.; Miyata, Y.; Suzuki, A.; Mori, T. (Pola Chemical Industries Inc.); 2-Nitroimidazole deriv., production thereof, and radiosensitizer containing the same as active ingredient. EP 0513351; JP 1991223258; US 5270330; WO 9111440 . |
| 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) | 54252 | (2R,3S)-1,2,3,4-butanetetrol | 149-32-6 | C4H10O4 | 详情 | 详情 |
| (II) | 54253 | (1R,2S)-3-(acetyloxy)-1-[(acetyloxy)methyl]-2-hydroxypropyl acetate | n/a | C10H16O7 | 详情 | 详情 |
| (III) | 54254 | (1R,2S)-3-(acetyloxy)-1-[(acetyloxy)methyl]-2-(methoxymethoxy)propyl acetate | n/a | C12H20O8 | 详情 | 详情 |
| (IV) | 54255 | (1R,2S)-3-(acetyloxy)-2-[(acetyloxy)methoxy]-1-[(acetyloxy)methyl]propyl acetate | n/a | C13H20O9 | 详情 | 详情 |
| (V) | 10145 | 2-Nitro-1H-imidazole; 2-Nitroimidazole | 527-73-1 | C3H3N3O2 | 详情 | 详情 |
| (VI) | 54256 | (1R,2S)-3-(acetyloxy)-1-[(acetyloxy)methyl]-2-[(2-nitro-1H-imidazol-1-yl)methoxy]propyl acetate | n/a | C14H19N3O9 | 详情 | 详情 |