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【结 构 式】

【分子编号】54254

【品名】(1R,2S)-3-(acetyloxy)-1-[(acetyloxy)methyl]-2-(methoxymethoxy)propyl acetate

【CA登记号】n/a

【 分 子 式 】C12H20O8

【 分 子 量 】292.286

【元素组成】C 49.31% H 6.9% O 43.79%

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:(III)

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
Extended Information