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【结 构 式】 
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【分子编号】19933 【品名】(2S)-2-([(2S)-2-[((2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-phenylpropanoyl)amino]-3-phenylpropanoyl]amino)propionic acid 【CA登记号】 |
【 分 子 式 】C26H34N4O5 【 分 子 量 】482.57992 【元素组成】C 64.71% H 7.1% N 11.61% O 16.58% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Title compound was synthesized by solid phase peptide synthesis on a Wang resin using N-9-fluorenylmethoxycarbonyl (Fmoc)-protected amino acids. The (Fmoc)alanine-resin (I) was treated with piperidine in N-methylpyrrolidone to yield deprotected alanine-resin (II). Then, condensation with (Fmoc)-phenylalanine (III) using diisopropyl cabodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) as the coupling reagents provided the (Fmoc)-dipeptide resin (IV), which was deprotected as before with piperidine in NMP. The resulting deprotected dipeptide resin (V) was submitted to further sequential amino acid coupling and deprotection cycles with (Fmoc)-phenylalanine (III), (Fmoc)-valine (VII), and (Fmoc)-leucine (IX), to yield in turn resins (VI), (VIII), and (X), respectively. Resin (X) was then coupled with cholic acid (XI) in the presence of DIC and HOBt to give the corresponding amide (XII).
| 【1】 Reed, M.J.; Hundal, A.; Molineaux, S.; Chin, J.; Kelley, M.; Findeis, M.A.; Kasman, L.; Benjamin, H.; Kubasek, W.; Musso, G.; Signer, E.R.; Wakefield, J.; Lee, J.-J.; Garnick, M.B.; Gefter, M.L. (Praecis Pharmaceuticals Inc.); Modulators of amyloid aggregation. JP 1999514333; WO 9628471 . |
| 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) | 19926 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C18H17NO4 | 详情 | 详情 | |
| (II) | 10141 | D-Alanine; D-2-Aminopropionic Acid | 338-69-2 | C3H7NO2 | 详情 | 详情 |
| (III) | 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 |
| (IV) | 19929 | (2S)-2-[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropanoyl)amino]propionic acid | C27H26N2O5 | 详情 | 详情 | |
| (V) | 19930 | (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]propionic acid | 3918-87-4 | C12H16N2O3 | 详情 | 详情 |
| (VI) | 19931 | (2S)-2-[((2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl)amino]propionic acid | C21H25N3O4 | 详情 | 详情 | |
| (VII) | 19932 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid | C20H21NO4 | 详情 | 详情 | |
| (VIII) | 19933 | (2S)-2-([(2S)-2-[((2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-phenylpropanoyl)amino]-3-phenylpropanoyl]amino)propionic acid | C26H34N4O5 | 详情 | 详情 | |
| (IX) | 19934 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-methylpentanoic acid | C21H23NO4 | 详情 | 详情 | |
| (X) | 19935 | (2S,5S,8S,11S,14S)-14-amino-5,8-dibenzyl-11-isopropyl-2,16-dimethyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaheptadecan-1-oic acid | C32H45N5O6 | 详情 | 详情 | |
| (XI) | 19936 | (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid | C24H40O5 | 详情 | 详情 | |
| (XII) | 19937 | (2S,5S,8S,11S,14S,19R)-5,8-dibenzyl-14-isobutyl-11-isopropyl-2-methyl-4,7,10,13,16-pentaoxo-19-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3,6,9,12,15-pentaazaicosan-1-oic acid | C56H83N5O10 | 详情 | 详情 |