allyl 4-[((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)[(2S)-2-amino-3-methylbutanoyl]amino]butanoate -Drug Synthesis Database

【结构式】

【分子编号】18853

【品名】allyl 4-[((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)[(2S)-2-amino-3-methylbutanoyl]amino]butanoate

【CA登记号】

【分子式】C₂₉H₄₆N₄O₆

【分子量】546.7076

【元素组成】C 63.71% H 8.48% N 10.25% O 17.56%

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：(VII)

Compound (XI) was prepared by solid phase peptide synthesis on a Rink amide 4-methylbenzhydrylamine (MBHA) resin. After removal of Fmoc protecting group from the resin with 20% piperidine in N-methyl-2-pyrrolidinone (NMP), a coupling cycle was carried out with Fmoc-Thr(O-t-Bu)OH (I) using bromotripyrrolidino phosphonium hexafluorophosphate (PyBroP) and diisopropylethylamine (DIEA) in NMP, followed by Fmoc removal with 20% piperidine in NMP. To the Thr-bound resin (II) they were stepwise coupled in subsequent coupling and deprotecting cycles the following amino acids: Fmoc- (N-allyloxycarbonylpropyl)PheOH (IV), Fmoc-ValCl (VI), Fmoc-Lys(Boc)OH (VIII), and Fmoc-D-TrpOH (X) to yield the corresponding peptide-bound resins (V), (VII), (IX) and (XI), respectively.

参考文献中间体

合成目标

【1】 Gilon, C.; et al.; A backbone-cyclic, receptor 5-selective somatostatin analogue: Synthesis, bioactivity, and nuclear magnetic resonance conformational analysis. J Med Chem 1998, 41, 6, 919.
【2】 Hornik, V.; Seri-Levy, A.; Gellerman, G.; Gilon, C. (Yissum Research Development Co.); Conformationally constrained backbone cyclized somatostatin analogs. WO 9804583 .

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)	18847	(2S,3R)-3-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butyric acid		C₂₃H₂₇NO₅	详情	详情
(II)	18848	9H-fluoren-9-ylmethyl (1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propylcarbamate		C₂₃H₂₈N₂O₄	详情	详情
(III)	18849	(2S,3R)-2-amino-3-(tert-butoxy)butanamide		C₈H₁₈N₂O₂	详情	详情
(IV)	18850	(2S)-2-[[4-(allyloxy)-4-oxobutyl][(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropionic acid		C₃₁H₃₁NO₆	详情	详情
(V)	18851	allyl 4-[((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)amino]butanoate		C₂₄H₃₇N₃O₅	详情	详情
(VI)	18852	9H-fluoren-9-ylmethyl (1S)-1-(chlorocarbonyl)-2-methylpropylcarbamate	103321-53-5	C₂₀H₂₀ClNO₃	详情	详情
(VII)	18853	allyl 4-[((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)[(2S)-2-amino-3-methylbutanoyl]amino]butanoate		C₂₉H₄₆N₄O₆	详情	详情
(VIII)	18854	(2S)-6-[(tert-butoxycarbonyl)amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid		C₂₆H₃₂N₂O₆	详情	详情
(IX)	18855	allyl (10S,13S)-10-amino-15-((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)-13-isopropyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazanonadecan-19-oate		C₄₀H₆₆N₆O₉	详情	详情
(X)	18856	(2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(1H-indol-3-yl)propionic acid		C₂₆H₂₂N₂O₄	详情	详情
(XI)	18857	allyl (10S,13S)-15-((1S)-2-[[(1S,2R)-1-(aminocarbonyl)-2-(tert-butoxy)propyl]amino]-1-benzyl-2-oxoethyl)-10-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-13-isopropyl-2,2-dimethyl-4,11,14-trioxo-3-oxa-5,12,15-triazanonadecan-19-oate		C₅₁H₇₆N₈O₁₀	详情	详情

Extended Information