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【结 构 式】

【分子编号】58840

【品名】ethyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(phenylselanyl)propanoyl](methyl)amino]acetate

【CA登记号】

【 分 子 式 】C19H28N2O5Se

【 分 子 量 】443.4018

【元素组成】C 51.47% H 6.36% N 6.32% O 18.04% Se 17.81%

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:(XXIII)

The tripeptide building block (XXVII) is prepared as follows. Cyclization of N-Boc-L-serine (XIX) to the beta-lactone (XX) is achieved by treatment with DEAD and PPh3. Subsequent ring opening with diphenyldiselenide in the presence of a reducing agent leads to selenide (XXI). Aminoacid (XXI) is then coupled to sarcosine ethyl ester (XXII) to afford dipeptide (XXIII). After acidic Boc group cleavage in (XXIII), the resultant carboxylic acid (XXIV) is coupled to N-Boc-D-aminobutyric acid (XXV) to give (XXVI). The N-Boc group of (XXVI) is then deprotected with trifluoroacetic acid, producing intermediate (XXVII).

1 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIX) 20126 (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid C8H15NO5 详情 详情
(XX) 58838 tert-butyl (3S)-2-oxooxetanylcarbamate C8H13NO4 详情 详情
(XXI) 58839 (2R)-2-[(tert-butoxycarbonyl)amino]-3-(phenylselanyl)propanoic acid C14H19NO4Se 详情 详情
(XXII) 32138 Sarcosine ethyl ester; Ethyl 2-(methylamino)acetate 52605-49-9 C5H11NO2 详情 详情
(XXIII) 58840 ethyl 2-[[(2R)-2-[(tert-butoxycarbonyl)amino]-3-(phenylselanyl)propanoyl](methyl)amino]acetate C19H28N2O5Se 详情 详情
(XXIV) 58841 ethyl 2-[[(2R)-2-amino-3-(phenylselanyl)propanoyl](methyl)amino]acetate C14H20N2O3Se 详情 详情
(XXV) 58842 (2R)-2-[(tert-butoxycarbonyl)amino]butanoic acid C9H17NO4 详情 详情
(XXVI) 58843 ethyl (6R,9R)-6-ethyl-2,2,11-trimethyl-4,7,10-trioxo-9-[(phenylselanyl)methyl]-3-oxa-5,8,11-triazatridecan-13-oate C23H35N3O6Se 详情 详情
(XXVII) 58844 ethyl 2-[[(2R)-2-{[(2R)-2-aminobutanoyl]amino}-3-(phenylselanyl)propanoyl](methyl)amino]acetate C18H27N3O4Se 详情 详情
Extended Information