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【结 构 式】 
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【分子编号】58847 【品名】(3S,6S,12R,15R)-1-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oic acid 【CA登记号】 |
【 分 子 式 】C47H54N10O9SSe 【 分 子 量 】1014.03376 【元素组成】C 55.67% H 5.37% N 13.81% O 14.2% S 3.16% Se 7.79% |
合成路线1
该中间体在本合成路线中的序号：(XXX)Basic hydrolysis of the precursor tetrapeptide ester (XVIII) provides acid (XXVIII). This is then coupled to the tripeptide ester (XXVII), leading to the linear peptide precursor (XXIX). Sequential hydrolysis in (XXIX) of the ethyl ester group with LiOH and the N-Boc group with trifluoroacetic acid produces aminoacid (XXX).
| 【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 |
|---|---|---|---|---|---|---|
| (XVIII) | 58837 | methyl 2-{[(2S)-2-{[(2S)-2-{[(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate | C37H43N7O8S | 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 | |
| (XXVIII) | 58845 | 2-{[(2S)-2-{[(2S)-2-{[(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)carbonyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetic acid | C36H41N7O8S | 详情 | 详情 | |
| (XXIX) | 58846 | ethyl (3S,6S,12R,15R)-1-(2-{(1R)-1-[(tert-butoxycarbonyl)amino]ethyl}-1,3-thiazol-4-yl)-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oate | C54H66N10O11SSe | 详情 | 详情 | |
| (XXX) | 58847 | (3S,6S,12R,15R)-1-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oic acid | C47H54N10O9SSe | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXX)Macrocyclization of aminoacid (XXX) in the presence of TBTU provides the cyclic peptide (XXXI). Conversion of the selenide group of (XXXI) to the target olefin is then accomplished by oxidation to selenoxide (XXXII) with sodium metaperiodate, followed by elimination in the presence of bicarbonate to produce the title compound.
| 【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 |
|---|---|---|---|---|---|---|
| (XXX) | 58847 | (3S,6S,12R,15R)-1-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-12-ethyl-3-(1H-indol-3-ylmethyl)-6-[(4-methoxy-1H-indol-3-yl)methyl]-17-methyl-1,4,7,10,13,16-hexaoxo-15-[(phenylselanyl)methyl]-2,5,8,11,14,17-hexaazanonadecan-19-oic acid | C47H54N10O9SSe | 详情 | 详情 | |
| (XXXI) | 58849 | (4S,7S,13R,16R,22R)-13-ethyl-4-(1H-indol-3-ylmethyl)-7-[(4-methoxy-1H-indol-3-yl)methyl]-18,22-dimethyl-16-[(phenylseleninyl)methyl]-24-thia-3,6,9,12,15,18,21,26-octaazabicyclo[21.2.1]hexacosa-1(25),23(26)-diene-2,5,8,11,14,17,20-heptone | C47H52N10O9SSe | 详情 | 详情 | |
| (XXXII) | 58850 | 4,8-Dimethyl-7-hydroxycoumarin | C11H10O3 | 详情 | 详情 |