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【结 构 式】 
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【分子编号】26291 【品名】methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-4-cyanobutanoate 【CA登记号】 |
【 分 子 式 】C14H16N2O4 【 分 子 量 】276.29212 【元素组成】C 60.86% H 5.84% N 10.14% O 23.16% |
合成路线1
该中间体在本合成路线中的序号：(XXX)Treatment of N-(benzyloxycarbonyl)-L-glutamine (XXVIII) with (trimethylsilyl)-diazomethane provided methyl ester (XXIX). Nitrile (XXX) was then obtained from (XXIX) by dehydration with cyanuryl chloride. Hydrolysis of the methyl ester of (XXX) with LiOH gave (XXXI), and hydrogenolysis of the carbobenzoxy group provided amino acid (XXXII). Alternatively, amino acid (XXXII) could be obtained by direct amide dehydration of (XXVIII) with Ac2O and pyridine, followed by transfer hydrogenolysis of the Cbz protecting group. Diazotization of amino acid (XXXII) with NaNO2 in the presence of H2SO4 then furnished (S)-2-hydroxy-4-cyanobutyric acid (XXXIII).
| 【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 23813 | 2,4,6-Trichloro-s-triazine; Cyanuric chloride; Trichlorocyanidine; Tricyanogen chloride; 2,4,6-Trichloro-1,3,5-triazine | 108-77-0 | C3Cl3N3 | 详情 | 详情 |
| (XXVIII) | 26289 | (2S)-5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid | C13H16N2O5 | 详情 | 详情 | |
| (XXIX) | 26290 | methyl (2S)-5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoate | C14H18N2O5 | 详情 | 详情 | |
| (XXX) | 26291 | methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-4-cyanobutanoate | C14H16N2O4 | 详情 | 详情 | |
| (XXXI) | 26292 | (2S)-2-[[(benzyloxy)carbonyl]amino]-4-cyanobutyric acid | C13H14N2O4 | 详情 | 详情 | |
| (XXXII) | 26293 | (2S)-2-amino-4-cyanobutyric acid | C5H8N2O2 | 详情 | 详情 | |
| (XXXIII) | 26294 | (2S)-4-cyano-2-hydroxybutyric acid | C5H7NO3 | 详情 | 详情 |