【结 构 式】 |
【分子编号】58841 【品名】ethyl 2-[[(2R)-2-amino-3-(phenylselanyl)propanoyl](methyl)amino]acetate 【CA登记号】 |
【 分 子 式 】C14H20N2O3Se 【 分 子 量 】343.28448 【元素组成】C 48.98% H 5.87% N 8.16% O 13.98% Se 23% |
合成路线1
该中间体在本合成路线中的序号:(XXIV)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 |