【结 构 式】 |
【分子编号】42130 【品名】(2R)-2-amino-3-[(4-methylbenzyl)sulfanyl]propionic acid 【CA登记号】42294-52-0 |
【 分 子 式 】C11H15NO2S 【 分 子 量 】225.31164 【元素组成】C 58.64% H 6.71% N 6.22% O 14.2% S 14.23% |
合成路线1
该中间体在本合成路线中的序号:(II)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).
【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 |