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【结 构 式】 
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【分子编号】30903 【品名】tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(Z)-(hydroxyamino)(methylsulfanyl)methylidene]amino]pentanoate 【CA登记号】 |
【 分 子 式 】C16H31N3O5S 【 分 子 量 】377.50536 【元素组成】C 50.91% H 8.28% N 11.13% O 21.19% S 8.49% |
合成路线1
该中间体在本合成路线中的序号：(VI)The fully protection of Nomega-(benzyloxycarbonyl)-L-ornithine (I) by usual methods gives Nomega-(benzyloxycarbonyl)-Nalpha-(tert-butoxycarbonyl)-L-ornithine tert-butyl ester (II), which is selectively deprotected at the omega amino group with H2 over Pd/C yielding the ornithine (III). The reaction of (III) with thiophosgene affords the isothiocyanate (IV), which is treated with hydroxylamine to afford the hydroxythiourea (V). The methylation of (V) with methyl iodide and NaH affords the S-methyl derivative (VI), which is finally deprotected with 4M HCl.
| 【1】 Ichimori, K.; Stuehr, D.J.; Synthesis and evaluation of new sulfur-containing L-arginine-derived inhibitors of nitric oxide synthase. J Med Chem 1999, 42, 10, 1842. |
| 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) | 30898 | (2S)-2-amino-5-[[(benzyloxy)carbonyl]amino]pentanoic acid | C13H18N2O4 | 详情 | 详情 | |
| (II) | 30899 | tert-butyl (2S)-5-[[(benzyloxy)carbonyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoate | C22H34N2O6 | 详情 | 详情 | |
| (III) | 30900 | tert-butyl (2S)-5-amino-2-[(tert-butoxycarbonyl)amino]pentanoate | C14H28N2O4 | 详情 | 详情 | |
| (IV) | 30901 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-isothiocyanatopentanoate | C15H26N2O4S | 详情 | 详情 | |
| (V) | 30902 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(hydroxyamino)carbothioyl]amino]pentanoate | C15H29N3O5S | 详情 | 详情 | |
| (VI) | 30903 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[[(Z)-(hydroxyamino)(methylsulfanyl)methylidene]amino]pentanoate | C16H31N3O5S | 详情 | 详情 |