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【结 构 式】

【分子编号】60111

【品名】methyl (3S)-1-((2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoyl)amino]-3-{3-[(tert-butoxycarbonyl)oxy]phenyl}propanoyl)hexahydro-3-pyridazinecarboxylate

【CA登记号】

【 分 子 式 】C33H44N4O9

【 分 子 量 】640.73392

【元素组成】C 61.86% H 6.92% N 8.74% O 22.47%

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:(XIV)

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
Extended Information