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【结 构 式】

【分子编号】26293

【品名】(2S)-2-amino-4-cyanobutyric acid

【CA登记号】

【 分 子 式 】C5H8N2O2

【 分 子 量 】128.1308

【元素组成】C 46.87% H 6.29% N 21.86% O 24.97%

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:(XXXII)

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
Extended Information