(2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-4-sulfanylbutanoyl)-6-hydroxy-2-piperidinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】50624

【品名】(2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-4-sulfanylbutanoyl)-6-hydroxy-2-piperidinecarboxylic acid

【CA登记号】

【分子式】C₁₈H₂₄N₂O₆S

【分子量】396.46444

【元素组成】C 54.53% H 6.1% N 7.07% O 24.21% S 8.09%

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：(IX)

The activation of N,N'-bis(benzyloxycarbonyl)-L-homocystine (I) with N-hydroxysuccinimide (II) by means of DCC gives the activated diester (III), which is condensed with N-(tert-butoxycarbonyl)-L-lysine (IV) by means of K2CO3, yielding the protected peptide (V). The selective deprotection of the epsilon amino groups of (V) by means of formic acid affords the dimeric peptide (VI), which is cleaved with dithiothreitol (DTT) to provide benzyloxycarbonyl-L-homocysteinyl-L-lysine (VII). The oxidation of (VII) with L-lysine epsilon aminotransferase (S. paucimobili or rec. E. coli) furnishes the formyl derivative (VIII), which is finally cyclized in acid medium to afford, through the nonisolated intermediate (IX), the target pyrido[2,1-b][1,3]thiazepine intermediate (X).

参考文献中间体

合成目标

【1】 Patel, R.N.; Enzymatic synthesis of chiral intermediates for omapatrilat, an antihypertensive drug. Biomol Eng 2001, 17, 6, 167.

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)	50614	(2S)-2-[[(benzyloxy)carbonyl]amino]-4-[((3S)-3-[[(benzyloxy)carbonyl]amino]-3-carboxypropyl)disulfanyl]butyric acid		C₂₄H₂₈N₂O₈S₂	详情	详情
(II)	10264	1-Hydroxydihydro-1H-pyrrole-2,5-dione; N-Hydroxysuccinimide; 1-Hydroxy-2,5-pyrrolidinedione	6066-82-6	C₄H₅NO₃	详情	详情
(III)	50618	benzyl (1S)-3-([(3S)-3-[[(benzyloxy)carbonyl]amino]-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-4-oxobutyl]disulfanyl)-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]propylcarbamate		C₃₂H₃₄N₄O₁₂S₂	详情	详情
(IV)	50619	N(epsilon)-Boc-L-lysine		C₁₁H₂₂N₂O₄	详情	详情
(V)	50620	(10S,13S,20S,23S)-13,20-bis[[(benzyloxy)carbonyl]amino]-23-[4-[(tert-butoxycarbonyl)amino]butyl]-10-carboxy-2,2-dimethyl-4,12,21-trioxo-3-oxa-16,17-dithia-5,11,22-triazatetracosan-24-oic acid		C₄₆H₆₈N₆O₁₄S₂	详情	详情
(VI)	50621	(5S,12S,15S)-15-(4-aminobutyl)-5-([[(1S)-5-amino-1-carboxypentyl]amino]carbonyl)-12-[[(benzyloxy)carbonyl]amino]-3,13-dioxo-1-phenyl-2-oxa-8,9-dithia-4,14-diazahexadecan-16-oic acid		C₃₆H₅₂N₆O₁₀S₂	详情	详情
(VII)	50622	(2S)-6-amino-2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-sulfanylbutanoyl)amino]hexanoic acid		C₁₈H₂₇N₃O₅S	详情	详情
(VIII)	50623	(2S)-2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-sulfanylbutanoyl)amino]-6-oxohexanoic acid		C₁₈H₂₄N₂O₆S	详情	详情
(IX)	50624	(2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-4-sulfanylbutanoyl)-6-hydroxy-2-piperidinecarboxylic acid		C₁₈H₂₄N₂O₆S	详情	详情
(X)	50617	(4S,7S,10aS)-4-[[(benzyloxy)carbonyl]amino]-5-oxooctahydro-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid		C₁₈H₂₂N₂O₅S	详情	详情

Extended Information