(3S,6S,9R,15R)-3,9-bis(4-aminobutyl)-1-[(2S)-1-((5S,8S)-5-(4-aminobutyl)-16-(4-chlorophenyl)-8-[[(2S)-2,6-diaminohexanoyl]amino]-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-anoyl)pyrrolidinyl]-6-[3-(cyclohexyloxy)-3-oxopropyl]-15-[[(4-methylbenzyl)s -Drug Synthesis Database

【结构式】

【分子编号】42143

【品名】(3S,6S,9R,15R)-3,9-bis(4-aminobutyl)-1-[(2S)-1-((5S,8S)-5-(4-aminobutyl)-16-(4-chlorophenyl)-8-[[(2S)-2,6-diaminohexanoyl]amino]-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-anoyl)pyrrolidinyl]-6-[3-(cyclohexyloxy)-3-oxopropyl]-15-[[(4-methylbenzyl)s

【CA登记号】

【分子式】C₇₀H₁₁₁ClN₁₄O₁₅S

【分子量】1456.2554

【元素组成】C 57.74% H 7.68% Cl 2.43% N 13.47% O 16.48% S 2.2%

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：(XVIII)

The title compound was obtained by solid-phase peptide synthesis starting from N-Boc-S-(4-methylbenzyl)cysteine linked to PAM resin (I). The protected peptide template (XVII) was synthesized by sequential coupling-deprotection cycles using the appropriate combination of either Boc- or Fmoc- N-alpha-protected amino acids. The following side-chain-protected amino acid residues were assembled: Gly (III), Lys(Boc) (V), Glu(cyclohexyl ester) (VII), Lys(Boc) (V), Pro (X), Gly (III), Lys(Boc) (V), Lys(chlorobenzyloxycarbonyl) (XIV) and Lys(Boc) (XVI) to produce the peptide resins (IV), (VI), (VIII), (IX), (XI), (XII), (XIII), (XV) and (XVII), respectively. Subsequent removal of the N-terminal and the four side-chain Boc protecting groups by means of trifluoroacetic acid yielded the peptide resin (XVIII).

参考文献中间体

合成目标

【1】 Callebaut, C.; et al.; Inhibition of HIV infection by pseudopeptides blocking viral envelope glycoprotein-mediated membrane fusion and cell death. Virology 1996, 218, 1, 181.

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)	42129	(2R)-2-[(tert-butoxycarbonyl)amino]-3-[(4-methylbenzyl)sulfanyl]propionic acid		C₁₆H₂₃NO₄S	详情	详情
(II)	42130	(2R)-2-amino-3-[(4-methylbenzyl)sulfanyl]propionic acid	42294-52-0	C₁₁H₁₅NO₂S	详情	详情
(III)	42131	2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]acetic acid	29022-11-5	C₁₇H₁₅NO₄	详情	详情
(IV)	42132	(2R)-2-[(2-aminoacetyl)amino]-3-[(4-methylbenzyl)sulfanyl]propionic acid		C₁₃H₁₈N₂O₃S	详情	详情
(V)	18854	(2S)-6-[(tert-butoxycarbonyl)amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid		C₂₆H₃₂N₂O₆	详情	详情
(VI)	42133	(10S,16R)-10-amino-2,2-dimethyl-16-[[(4-methylbenzyl)sulfanyl]methyl]-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid		C₂₄H₃₈N₄O₆S	详情	详情
(VII)	42134	(2S)-5-(cyclohexyloxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid	150047-85-1	C₂₆H₂₉NO₆	详情	详情
(VIII)	42135	(10R,16R)-10-[(3S)-3-amino-6-(cyclohexyloxy)-2,6-dioxohexyl]-2,2-dimethyl-16-[[(4-methylbenzyl)sulfanyl]methyl]-4,11,14-trioxo-3-oxa-5,12,15-triazaheptadecan-17-oic acid		C₃₆H₅₆N₄O₉S	详情	详情
(IX)	42136	(10S,13S,16R,22R)-10-amino-16-[4-[(tert-butoxycarbonyl)amino]butyl]-13-[3-(cyclohexyloxy)-3-oxopropyl]-2,2-dimethyl-22-[[(4-methylbenzyl)sulfanyl]methyl]-4,11,14,17,20-pentaoxo-3-oxa-5,12,18,21-tetraazatricosan-23-oic acid		C₄₇H₇₆N₆O₁₂S	详情	详情
(X)	34762	(2S)-1-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-pyrrolidinecarboxylic acid	71989-31-6	C₂₀H₁₉NO₄	详情	详情
(XI)	42137	(10S,13S,16R,22R)-16-[4-[(tert-butoxycarbonyl)amino]butyl]-13-[3-(cyclohexyloxy)-3-oxopropyl]-2,2-dimethyl-22-[[(4-methylbenzyl)sulfanyl]methyl]-4,11,14,17,20-pentaoxo-10-[[(2S)pyrrolidinylcarbonyl]amino]-3-oxa-5,12,18,21-tetraazatricosan-23-oic acid		C₅₂H₈₃N₇O₁₃S	详情	详情
(XII)	42138	(10S,13S,16R,22R)-10-([[(2S)-1-(2-aminoacetyl)pyrrolidinyl]carbonyl]amino)-16-[4-[(tert-butoxycarbonyl)amino]butyl]-13-[3-(cyclohexyloxy)-3-oxopropyl]-2,2-dimethyl-22-[[(4-methylbenzyl)sulfanyl]methyl]-4,11,14,17,20-pentaoxo-3-oxa-5,12,18,21-tetraaz		C₅₄H₈₆N₈O₁₄S	详情	详情
(XIII)	42139	(10S,13S,16R,22R)-10-[([(2S)-1-[2-([(2S)-2-amino-6-[(tert-butoxycarbonyl)amino]hexanoyl]amino)acetyl]pyrrolidinyl]carbonyl)amino]-16-[4-[(tert-butoxycarbonyl)amino]butyl]-13-[3-(cyclohexyloxy)-3-oxopropyl]-2,2-dimethyl-22-[[(4-methylbenzyl)sulfanyl]		C₆₅H₁₀₆N₁₀O₁₇S	详情	详情
(XIV)	42140	(2S)-6-([[(4-chlorobenzyl)oxy]carbonyl]amino)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid		C₂₉H₂₉ClN₂O₆	详情	详情
(XV)	42141	(10S,13S,16R,22R)-10-[([(2S)-1-[(5S,8S)-8-amino-5-[4-[(tert-butoxycarbonyl)amino]butyl]-16-(4-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-anoyl]pyrrolidinyl]carbonyl)amino]-16-[4-[(tert-butoxycarbonyl)amino]butyl]-13-[3-(cyclohexyloxy)		C₇₉H₁₂₃ClN₁₂O₂₀S	详情	详情
(XVI)	37991	(2S)-2,6-bis[(tert-butoxycarbonyl)amino]hexanoic acid	2483-46-7	C₁₆H₃₀N₂O₆	详情	详情
(XVII)	42142	(10S,13S,16R,22R)-10-[[((2S)-1-[(5S,8S,11S)-11-[(tert-butoxycarbonyl)amino]-5-[4-[(tert-butoxycarbonyl)amino]butyl]-8-[4-([[(4-chlorobenzyl)oxy]carbonyl]amino)butyl]-19,19-dimethyl-4,7,10,17-tetraoxo-18-oxa-3,6,9,16-tetraazaicos-1-anoyl]pyrrolidinyl		C₉₅H₁₅₁ClN₁₄O₂₅S	详情	详情
(XVIII)	42143	(3S,6S,9R,15R)-3,9-bis(4-aminobutyl)-1-[(2S)-1-((5S,8S)-5-(4-aminobutyl)-16-(4-chlorophenyl)-8-[[(2S)-2,6-diaminohexanoyl]amino]-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-anoyl)pyrrolidinyl]-6-[3-(cyclohexyloxy)-3-oxopropyl]-15-[[(4-methylbenzyl)s		C₇₀H₁₁₁ClN₁₄O₁₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVIII)

Simultaneous coupling of five N-Boc-arginin (XIX) residues to the free amino groups of the peptide template (XVIII), followed by acid deprotection of the Boc groups, furnished (XX). To this were assembled five N-Boc-proline residues (XXI) to provide, after acid deprotection, resin (XXII). Then, reductive condensation with Boc-protected lysinal (XXIII) furnished the protected pseudopeptide adduct (XXIV). Finally, simultaneous cleavage from the resin and removal of protecting groups was effected by treatment with anhydrous hydrogen fluoride.

参考文献中间体

合成目标

【1】 Callebaut, C.; et al.; Inhibition of HIV infection by pseudopeptides blocking viral envelope glycoprotein-mediated membrane fusion and cell death. Virology 1996, 218, 1, 181.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVIII)	42143	(3S,6S,9R,15R)-3,9-bis(4-aminobutyl)-1-[(2S)-1-((5S,8S)-5-(4-aminobutyl)-16-(4-chlorophenyl)-8-[[(2S)-2,6-diaminohexanoyl]amino]-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-anoyl)pyrrolidinyl]-6-[3-(cyclohexyloxy)-3-oxopropyl]-15-[[(4-methylbenzyl)s		C₇₀H₁₁₁ClN₁₄O₁₅S	详情	详情
(XIX)	14073	(2S)-5-[[Amino(imino)methyl]amino]-2-[(tert-butoxycarbonyl)amino]pentanoic acid	13726-76-6	C₁₁H₂₂N₄O₄	详情	详情
(XX)	42144			C₁₀₀H₁₇₁ClN₃₄O₂₄S	详情	详情
(XXI)	16734	(2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid		C₁₀H₁₇NO₄	详情	详情
(XXII)	42145			C₈₁H₁₂₆ClN₁₉O₁₇SArg₄Pro₄	详情	详情
(XXIII)	42146	tert-butyl (1S)-5-[(tert-butoxycarbonyl)amino]-1-formylpentylcarbamate		C₁₆H₃₀N₂O₅	详情	详情
(XXIV)	42147			C₂₀₅H₃₅₀ClN₅₃O₅₀S	详情	详情

Extended Information