【结 构 式】 |
【分子编号】60107 【品名】(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3-hydroxyphenyl)propanoic acid 【CA登记号】 |
【 分 子 式 】C17H17NO5 【 分 子 量 】315.32572 【元素组成】C 64.75% H 5.43% N 4.44% O 25.37% |
合成路线1
该中间体在本合成路线中的序号:(IX)Chiral tripeptide intermediate (XV): The deprotection of perhydropyridazine carboxylic acid methyl ester (VII) with TFA in dichloromethane gives ester (VIII), which is condensed with N-(benzyloxycarbonyl)-3-hydroxy-L-tyrosine (IX) by means of HBTU and TEA in acetonitrile to yield the dipeptide (X). The protection of the phenolic OH group of (X) with Boc2O and TEA In dichloromethane affords (XI), which is selectively deprotected with H2 over Pd/C in ethanol to provide dipeptide (XII). The condensation of (XII) with N-(benzyloxycarbonyl)-L-valine (XIII) by means of HBTU as before gives the protected tripeptide (XIV), which is finally treated with H2 over Pd/C in ethanol to provide the target tripeptide intermediate (XV)
【1】 Duan, M.S.; Paquette, L.A.; Enantioselective total synthesis of the cyclophilin-binding immunosuppressive agent sanglifehrin A. Angew Chem. Int Ed 2001, 40, 19, 3632. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VII) | 60105 | 1,2-di(tert-butyl) 3-methyl (3S)tetrahydro-1,2,3-pyridazinetricarboxylate | C16H28N2O6 | 详情 | 详情 | |
(VIII) | 60106 | methyl (3S)hexahydro-3-pyridazinecarboxylate | C6H12N2O2 | 详情 | 详情 | |
(IX) | 60107 | (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3-hydroxyphenyl)propanoic acid | C17H17NO5 | 详情 | 详情 | |
(X) | 60108 | methyl (3S)-1-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(3-hydroxyphenyl)propanoyl]hexahydro-3-pyridazinecarboxylate | C23H27N3O6 | 详情 | 详情 | |
(XI) | 60109 | methyl (3S)-1-((2S)-2-{[(benzyloxy)carbonyl]amino}-3-{3-[(tert-butoxycarbonyl)oxy]phenyl}propanoyl)hexahydro-3-pyridazinecarboxylate | C28H35N3O8 | 详情 | 详情 | |
(XII) | 60110 | methyl (3S)-1-((2S)-2-amino-3-{3-[(tert-butoxycarbonyl)oxy]phenyl}propanoyl)hexahydro-3-pyridazinecarboxylate | C20H29N3O6 | 详情 | 详情 | |
(XIII) | 49332 | (2R)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid | C13H17NO4 | 详情 | 详情 | |
(XIV) | 60111 | methyl (3S)-1-((2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)amino]-3-{3-[(tert-butoxycarbonyl)oxy]phenyl}propanoyl)hexahydro-3-pyridazinecarboxylate | C33H44N4O9 | 详情 | 详情 | |
(XV) | 60112 | methyl (3S)-1-((2S)-2-{[(2S)-2-amino-3-methylbutanoyl]amino}-3-{3-[(tert-butoxycarbonyl)oxy]phenyl}propanoyl)hexahydro-3-pyridazinecarboxylate | C25H38N4O7 | 详情 | 详情 |