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【结 构 式】 
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【分子编号】65165 【品名】benzyl (6S,9S,15S,18S,21S,24S,27S)-15,21-dibenzyl-24-[(1R)-1-(benzyloxy)ethyl]-9,27-diisobutyl-18-isopropyl-2,2-dimethyl-6-[(1S)-1-methylpropyl]-4,7,10,13,16,19,22,25-octaoxo-3-oxa-5,8,11,14,17,20,23,26-octaazaoctacosan-28-oate 【CA登记号】 |
【 分 子 式 】C66H92N8O12 【 分 子 量 】1189.5032 【元素组成】C 66.64% H 7.8% N 9.42% O 16.14% |
合成路线1
该中间体在本合成路线中的序号：(XXII)Coupling of N-Boc-L-leucine (XVII) with glycine benzyl ester (XVIII), followed by acidic N-Boc group cleavage, affords the dipeptide benzyl ester (XIX), which is submitted to coupling with N-Boc-L-isoleucine (XX) and further benzyl ester hydrogenolysis to give rise to the N-Boc tripeptide (XXI). Then, assembly between (XXI) and pentapeptide (XVI) is accomplished by means of EDC/HOBt, providing the protected peptide (XXII). Hydrogenolysis of the benzyl groups of (XXII), followed by Boc group cleavage with trifluoroacetic acid, leads to the fully deprotected octapeptide (XXIII).
| 【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 |
|---|---|---|---|---|---|---|
| (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 | |
| (XVII) | 23663 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine | C11H21NO4 | 详情 | 详情 | |
| (XVIII) | 13601 | benzyl 2-aminoacetate; Glycine benzyl ester hydrochloride | 1738-68-7 | C9H11NO2 | 详情 | 详情 |
| (XIX) | 65167 | benzyl 2-{[(2S)-2-amino-4-methylpentanoyl]amino}acetate | C15H22N2O3 | 详情 | 详情 | |
| (XX) | 30009 | (2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoic acid | 13139-16-7 | C11H21NO4 | 详情 | 详情 |
| (XXI) | 65166 | (6S,9S)-9-isobutyl-2,2-dimethyl-6-[(1S)-1-methylpropyl]-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oic acid | C19H35N3O6 | 详情 | 详情 | |
| (XXII) | 65165 | benzyl (6S,9S,15S,18S,21S,24S,27S)-15,21-dibenzyl-24-[(1R)-1-(benzyloxy)ethyl]-9,27-diisobutyl-18-isopropyl-2,2-dimethyl-6-[(1S)-1-methylpropyl]-4,7,10,13,16,19,22,25-octaoxo-3-oxa-5,8,11,14,17,20,23,26-octaazaoctacosan-28-oate | C66H92N8O12 | 详情 | 详情 | |
| (XXIII) | 65164 | (2S,5S,8S,11S,14S,20S,23S,24S)-23-amino-8,14-dibenzyl-5-[(1R)-1-hydroxyethyl]-2,20-diisobutyl-11-isopropyl-24-methyl-4,7,10,13,16,19,22-heptaoxo-3,6,9,12,15,18,21-heptaazahexacosan-1-oic acid | C47H72N8O10 | 详情 | 详情 |