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【结 构 式】

【分子编号】19929

【品名】(2S)-2-[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropanoyl)amino]propionic acid

【CA登记号】

【 分 子 式 】C27H26N2O5

【 分 子 量 】458.51392

【元素组成】C 70.73% H 5.72% N 6.11% O 17.45%

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:(IV)

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
Extended Information