benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate -Drug Synthesis Database

【结构式】

【分子编号】65159

【品名】benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate

【CA登记号】

【分子式】C₃₃H₄₁N₃O₅

【分子量】559.70576

【元素组成】C 70.82% H 7.38% N 7.51% O 14.29%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(XII)

Coupling between N-Boc-O-benzyl-L-threonine (VII) and L-leucine benzyl ester (VIII) by means of DCC/HOBt gives the protected dipeptide (IX). Subsequent N-Boc group cleavage in (IX) upon treatment with formic acid yields (X). Further coupling of dipeptide (X) with N-Boc-L-phenylalanine (XI), followed by formic acid deprotection, leads to the benzyl-protected tripeptide (XII).

参考文献中间体

合成目标

【1】 Rawale, S.; Hrihorczuk, L.M.; Wei, W.-Z.; Zemlicka, J.; Synthesis and biological activity of the prodrug of class I major histocompatibility peptide GILGFVFTL activated by Beta-glucuronidase. J Med Chem 2002, 45, 4, 937.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	50782	(2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butyric acid		C₁₆H₂₃NO₅	详情	详情
(VIII)	22252	Benzyl (2S)-2-amino-4-methylpentanoate; Benzyl (S)-leucinate		C₁₃H₁₉NO₂	详情	详情
(IX)	65160	benzyl (2S)-2-({(2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butanoyl}amino)-4-methylpentanoate		C₂₉H₄₀N₂O₆	详情	详情
(X)	65158	benzyl (2S)-2-{[(2S,3R)-2-amino-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate		C₂₄H₃₂N₂O₄	详情	详情
(XI)	12874	(2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine	13734-34-4	C₁₄H₁₉NO₄	详情	详情
(XII)	65159	benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate		C₃₃H₄₁N₃O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XII)

In a similar fashion, N-Boc-L-phenylalanine (XI) is coupled with L-valine benzyl ester (XIII) to furnish the protected dipeptide (XIV). Debenzylation of (XIV) with H2 and Pd/C leads to acid (XV), which is then condensed with tripeptide (XII) to yield, after deprotection with formic acid, the pentapeptide derivative (XVI).

参考文献中间体

合成目标

【1】 Rawale, S.; Hrihorczuk, L.M.; Wei, W.-Z.; Zemlicka, J.; Synthesis and biological activity of the prodrug of class I major histocompatibility peptide GILGFVFTL activated by Beta-glucuronidase. J Med Chem 2002, 45, 4, 937.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	12874	(2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine	13734-34-4	C₁₄H₁₉NO₄	详情	详情
(XII)	65159	benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate		C₃₃H₄₁N₃O₅	详情	详情
(XIII)	41936	benzyl (2S)-2-amino-3-methylbutanoate		C₁₂H₁₇NO₂	详情	详情
(XIV)	65162	benzyl (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-methylbutanoate		C₂₆H₃₄N₂O₅	详情	详情
(XV)	65163	(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-methylbutanoic acid		C₁₉H₂₈N₂O₅	详情	详情
(XVI)	65161	benzyl (2S,5S,8S,11S,14S)-14-amino-8-benzyl-5-[(1R)-1-(benzyloxy)ethyl]-2-isobutyl-11-isopropyl-4,7,10,13-tetraoxo-15-phenyl-3,6,9,12-tetraazapentadecan-1-oate		C₄₇H₅₉N₅O₇	详情	详情

Extended Information