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【结 构 式】

【分子编号】65159

【品名】benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate

【CA登记号】

【 分 子 式 】C33H41N3O5

【 分 子 量 】559.70576

【元素组成】C 70.82% H 7.38% N 7.51% O 14.29%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XII)

Coupling between N-Boc-O-benzyl-L-threonine (VII) and L-leucine benzyl ester (VIII) by means of DCC/HOBt gives the protected dipeptide (IX). Subsequent N-Boc group cleavage in (IX) upon treatment with formic acid yields (X). Further coupling of dipeptide (X) with N-Boc-L-phenylalanine (XI), followed by formic acid deprotection, leads to the benzyl-protected tripeptide (XII).

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
(VII) 50782 (2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butyric acid C16H23NO5 详情 详情
(VIII) 22252 Benzyl (2S)-2-amino-4-methylpentanoate; Benzyl (S)-leucinate C13H19NO2 详情 详情
(IX) 65160 benzyl (2S)-2-({(2S,3R)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]butanoyl}amino)-4-methylpentanoate C29H40N2O6 详情 详情
(X) 65158 benzyl (2S)-2-{[(2S,3R)-2-amino-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate C24H32N2O4 详情 详情
(XI) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(XII) 65159 benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate C33H41N3O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XII)

In a similar fashion, N-Boc-L-phenylalanine (XI) is coupled with L-valine benzyl ester (XIII) to furnish the protected dipeptide (XIV). Debenzylation of (XIV) with H2 and Pd/C leads to acid (XV), which is then condensed with tripeptide (XII) to yield, after deprotection with formic acid, the pentapeptide derivative (XVI).

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
(XI) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(XII) 65159 benzyl (2S)-2-{[(2S,3R)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-(benzyloxy)butanoyl]amino}-4-methylpentanoate C33H41N3O5 详情 详情
(XIII) 41936 benzyl (2S)-2-amino-3-methylbutanoate C12H17NO2 详情 详情
(XIV) 65162 benzyl (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-methylbutanoate C26H34N2O5 详情 详情
(XV) 65163 (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-methylbutanoic acid C19H28N2O5 详情 详情
(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
Extended Information