(2S)-2-({(2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】56123

【品名】(2S)-2-({(2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid

【CA登记号】

【分子式】C₁₄H₂₇N₃O₅

【分子量】317.3856

【元素组成】C 52.98% H 8.57% N 13.24% O 25.2%

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：(VIII)

The monocyclic peptide precursor (XVIII) was prepared by solid-phase peptide synthesis by two different sequences. In the first one, N-Fmoc-L-leucine (IV) was linked to chlorotrityl resin, and the resultant resin-bound Fmoc-leucine (V) was subsequently deprotected by treatment with piperidine in DMF. To the deprotected leucine-resin (VI) was attached the diaminopropionic acid derivative (III), using either dicyclohexylcarbodiimide or diisopropylcarbodiimide as the coupling reagents, to yield the dipeptide resin (VII), which was further deprotected to (VIII) by means of piperidine in DMF.

参考文献中间体

合成目标

【1】 Aimoto, S.; Akaji, K.; Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent. Tetrahedron 2001, 57, 9, 1749.
【2】 Arcamone, F.; Maggi, C.A.; Quartara, L.; Giannotti, D. (Menarini Industrie Farma Riunite Srl); Bicyclic tachykinins antagonists, preparation thereof and their use in pharmaceutical compsn.. JP 1999501643; WO 9628467 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV),(V)	19934	(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoic acid		C₂₁H₂₃NO₄	详情	详情
(III)	56121	(2S)-3-[(tert-butoxycarbonyl)amino]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid		C₂₃H₂₆N₂O₆	详情	详情
(VI)	26057	L-Leucine	61-90-5	C₆H₁₃NO₂	详情	详情
(VII)	56122	(2S)-2-[((2S)-3-[(tert-butoxycarbonyl)amino]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoyl)amino]-4-methylpentanoic acid		C₂₉H₃₇N₃O₇	详情	详情
(VIII)	56123	(2S)-2-({(2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid		C₁₄H₂₇N₃O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

To the resin (VIII) were in turn incorporated the following aminoacids: N-Fmoc-L-phenylalanine (IX), N-Fmoc-tryptophan (XI), N-Fmoc-L-aspartic acid beta-t-butyl ester (XIII) and the glycosylated asparragine derivative (XV), each followed by an Fmoc deprotection step to furnish the peptide resins (X), (XII), (XIV) and (XVI), respectively.

参考文献中间体

合成目标

【1】 Aimoto, S.; Akaji, K.; Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent. Tetrahedron 2001, 57, 9, 1749.
【2】 Arcamone, F.; Maggi, C.A.; Quartara, L.; Giannotti, D. (Menarini Industrie Farma Riunite Srl); Bicyclic tachykinins antagonists, preparation thereof and their use in pharmaceutical compsn.. JP 1999501643; WO 9628467 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	56123	(2S)-2-({(2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid		C₁₄H₂₇N₃O₅	详情	详情
(IX)	19030	(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropionic acid; N-((9H-fluoren-9-ylmethoxy)carbonyl)-phenylalanine	35661-40-6	C₂₄H₂₁NO₄	详情	详情
(X)	56124	(2S)-2-({(2S)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid		C₂₃H₃₆N₄O₆	详情	详情
(XI)	56129	(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoic acid		C₂₆H₂₂N₂O₄	详情	详情
(XII)	56125	(2S)-2-({(2S)-2-[((2S)-2-{[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoyl)amino]-3-[(tert-butoxycarbonyl)amino]propanoyl}amino)-4-methylpentanoic acid		C₃₄H₄₆N₆O₇	详情	详情
(XIII)	22260	(2S)-4-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutyric acid		C₂₃H₂₅NO₆	详情	详情
(XIV)	56126	(2S,5S,8S,11S,14S)-14-amino-8-benzyl-5-{[(tert-butoxycarbonyl)amino]methyl}-11-(1H-indol-3-ylmethyl)-2-isobutyl-18,18-dimethyl-4,7,10,13,16-pentaoxo-17-oxa-3,6,9,12-tetraazanonadecan-1-oic acid		C₄₂H₅₉N₇O₁₀	详情	详情
(XV)	56127	2,3,4,5,6-pentafluorophenyl (2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxobutanoate		C₃₉H₃₆F₅N₃O₁₃	详情	详情
(XVI)	56128	(2S,5S,8S,11S,14S)-14-{[(2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-amino-4-oxobutanoyl]amino}-8-benzyl-5-{[(tert-butoxycarbonyl)amino]methyl}-11-(1H-indol-3-ylmethyl)-2-isobutyl-18,18-dimethyl-4,7,10,13,16-pentaoxo-17-oxa-3,6,9,12-tetraazanonadecan-1-oic acid		C₆₀H₈₄N₁₀O₂₀	详情	详情

Extended Information