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【结 构 式】 
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【分子编号】27060 【品名】tert-butyl (1S)-1-[(1-benzyl-1H-imidazol-2-yl)(hydroxy)methyl]-3-methylbutylcarbamate 【CA登记号】 |
【 分 子 式 】C21H31N3O3 【 分 子 量 】373.49556 【元素组成】C 67.53% H 8.37% N 11.25% O 12.85% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of tert-butoxycarbonyl-L-leucinal (I) with 1-benzylimidazole (II) by means of BuLi in THF gives 1-benzyl-2-[2(S)-(tert-butoxycarbonylamino)-1-hydroxy-4-methylpentyl]imidazole (III), which is hydrolyzed with HCl in dioxane yielding 2-(2(S)-amino)-1-hydroxy-4-methylpentyl]-2-benzylimidazole (IV). The condensation of (IV) with tert-butoxycarbonyl-L-leucine (V) by means of dicyclohexylcarbodiimide (DCC) and hydroxybenzotriazole (HOBT) in TFA/dichloromethane affords the protected seudo-dipeptide (VI), which is debenzylated with H2 over Pd/C giving the expected seudo-peptide (VII): Finally, this compound is oxidizad with the Dess-Martin oxidant.
| 【1】 Tao, M.; et al.; Inhibition of calpain by peptidyl heterocycles. Bioorg Med Chem Lett 1996, 6, 24, 3009. |
| 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) | 27058 | tert-butyl (1S)-1-formyl-3-methylbutylcarbamate | C11H21NO3 | 详情 | 详情 | |
| (II) | 27059 | 1-benzyl-1H-imidazole | 4238-71-5 | C10H10N2 | 详情 | 详情 |
| (III) | 27060 | tert-butyl (1S)-1-[(1-benzyl-1H-imidazol-2-yl)(hydroxy)methyl]-3-methylbutylcarbamate | C21H31N3O3 | 详情 | 详情 | |
| (IV) | 27061 | (2S)-2-amino-1-(1-benzyl-1H-imidazol-2-yl)-4-methyl-1-pentanol | C16H23N3O | 详情 | 详情 | |
| (V) | 23663 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine | C11H21NO4 | 详情 | 详情 | |
| (VI) | 27062 | tert-butyl (1S)-1-[([(1S)-1-[(1-benzyl-1H-imidazol-2-yl)(hydroxy)methyl]-3-methylbutyl]amino)carbonyl]-3-methylbutylcarbamate | C27H42N4O4 | 详情 | 详情 | |
| (VII) | 27063 | tert-butyl (1S)-1-[([(1S)-1-[hydroxy(1H-imidazol-2-yl)methyl]-3-methylbutyl]amino)carbonyl]-3-methylbutylcarbamate | C20H36N4O4 | 详情 | 详情 |