benzyl (2S)-2-({(2S)-2-[((2S)-5-amino-2-{[(2S)-2-amino-2-cyclohexylethanoyl]amino}-5-oxopentanoyl)amino]-3-hydroxypropanoyl}amino)-4-methylpentanoate -Drug Synthesis Database

【结构式】

【分子编号】53686

【品名】benzyl (2S)-2-({(2S)-2-[((2S)-5-amino-2-{[(2S)-2-amino-2-cyclohexylethanoyl]amino}-5-oxopentanoyl)amino]-3-hydroxypropanoyl}amino)-4-methylpentanoate

【CA登记号】n/a

【分子式】C₂₉H₄₅N₅O₇

【分子量】575.7058

【元素组成】C 60.5% H 7.88% N 12.16% O 19.45%

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：(XXXVII)

Coupling between N-Boc-L-serine (XXIX) and L-leucine benzyl ester (XXX) furnished the Boc-dipeptide (XXXI), which was deprotected by means of a solution of HCl in isopropyl acetate. The resultant seryl-leucine benzyl ester (XXXII) was condensed with N-Boc-L-glutamine (XXXIII) to afford (XXXIV), which after N-Boc deprotection yielded tripeptide ester (XXXV). Further coupling of (XXXV) with N-Boc-L-cyclohexylglycine (XXXVI), followed by acidic deprotection, gave tetrapeptide (XXXVII). This was finally acylated with the glutaryl tripeptide (XXVIII) to provide the desired peptide intermediate (XVII).

参考文献中间体

合成目标

【1】 Kaufman, M.J.; Almarsson, O.; Nerurkar, M.J.; Lynch, J.E.; Karki, S.B.; Cameron, M.; Lieberman, D.R.; Robbins, M.A.; Shi, Y.-J. (Merck & Co., Inc.); Salt form of a conjugate useful in the treatment of prostate cancer. US 6355611; WO 0130804 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVII)	53673	(3S,6S,9S,12S,15S,18S)-12-(3-amino-3-oxopropyl)-9-cyclohexyl-1-{(2S,4R)-1-[5-(9H-fluoren-9-ylmethoxy)-5-oxopentanoyl]-4-hydroxypyrrolidinyl}-6,15-bis(hydroxymethyl)-18-isobutyl-3-methyl-1,4,7,10,13,16-hexaoxo-2,5,8,11,14,17-hexaazanonadecan-19-oic acid	n/a	C₅₂H₇₂N₈O₁₅	详情	详情
(XXVIII)	53682	(2S)-2-({(2S)-2-[({(2S,4R)-1-[5-(9H-fluoren-9-ylmethoxy)-5-oxopentanoyl]-4-hydroxypyrrolidinyl}carbonyl)amino]propanoyl}amino)-3-hydroxypropanoic acid	n/a	C₃₀H₃₅N₃O₉	详情	详情
(XXIX)	20126	(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid		C₈H₁₅NO₅	详情	详情
(XXX)	22252	Benzyl (2S)-2-amino-4-methylpentanoate; Benzyl (S)-leucinate		C₁₃H₁₉NO₂	详情	详情
(XXXI)	53672	benzyl (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoyl}amino)-4-methylpentanoate	n/a	C₂₁H₃₂N₂O₆	详情	详情
(XXXII)	53683	benzyl (2S)-2-{[(2S)-2-amino-3-hydroxypropanoyl]amino}-4-methylpentanoate	n/a	C₁₆H₂₄N₂O₄	详情	详情
(XXXIII)	31820	(2S)-5-amino-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid	13726-85-7	C₁₀H₁₈N₂O₅	详情	详情
(XXXIV)	53684	benzyl (6S,9S,12S)-6-(3-amino-3-oxopropyl)-9-(hydroxymethyl)-12-isobutyl-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate	n/a	C₂₆H₄₀N₄O₈	详情	详情
(XXXV)	53685	benzyl (2S)-2-[((2S)-2-{[(2S)-2,5-diamino-5-oxopentanoyl]amino}-3-hydroxypropanoyl)amino]-4-methylpentanoate	n/a	C₂₁H₃₂N₄O₆	详情	详情
(XXXVI)	35619	(2S)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoic acid		C₁₃H₂₃NO₄	详情	详情
(XXXVII)	53686	benzyl (2S)-2-({(2S)-2-[((2S)-5-amino-2-{[(2S)-2-amino-2-cyclohexylethanoyl]amino}-5-oxopentanoyl)amino]-3-hydroxypropanoyl}amino)-4-methylpentanoate	n/a	C₂₉H₄₅N₅O₇	详情	详情

Extended Information