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【结 构 式】 
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【分子编号】26299 【品名】tert-butyl (2S)-2-[((2S,4R)-2-[[(2S)-4-cyano-2-hydroxybutanoyl]amino]-4-methyloctanoyl)(methyl)amino]-4-methylpentanoate 【CA登记号】 |
【 分 子 式 】C25H45N3O5 【 分 子 量 】467.64952 【元素组成】C 64.21% H 9.7% N 8.99% O 17.11% |
合成路线1
该中间体在本合成路线中的序号：(XXXVIII)Treatment of N-Boc-N-methyl-L-leucine (XXXIV) with isobutene and H2SO4 in CH2Cl2 generated tert-butyl ester (XXXV) with simultaneous removal of the Boc group. Subsequent coupling of (XXXV) with N-Boc-5-propyl-L-leucine (X) utilizing EDC and HOAt provided dipeptide (XXXVI). Selective removal of the N-Boc group of (XXXVI) was accomplished by treatment with formic acid at r.t. The resulting amine (XXXVII) was then coupled with hydroxyacid (XXXIII) to yield the target tripeptide (XXXVIII).
| 【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 26272 | (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-methyloctanoic acid | C14H27NO4 | 详情 | 详情 | |
| (XXXIII) | 26294 | (2S)-4-cyano-2-hydroxybutyric acid | C5H7NO3 | 详情 | 详情 | |
| (XXXIV) | 26295 | (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-4-methylpentanoic acid | 609-23-4 | C12H23NO4 | 详情 | 详情 |
| (XXXV) | 26296 | tert-butyl (2S)-4-methyl-2-(methylamino)pentanoate | C11H23NO2 | 详情 | 详情 | |
| (XXXVI) | 26297 | tert-butyl (2S)-2-[[(2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-methyloctanoyl](methyl)amino]-4-methylpentanoate | C25H48N2O5 | 详情 | 详情 | |
| (XXXVII) | 26298 | tert-butyl (2S)-2-[[(2S,4R)-2-amino-4-methyloctanoyl](methyl)amino]-4-methylpentanoate | C20H40N2O3 | 详情 | 详情 | |
| (XXXVIII) | 26299 | tert-butyl (2S)-2-[((2S,4R)-2-[[(2S)-4-cyano-2-hydroxybutanoyl]amino]-4-methyloctanoyl)(methyl)amino]-4-methylpentanoate | C25H45N3O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXXVIII)The condensation of tetrapeptide (XLVI) with tripeptide alcohol (XXXVIII) under modified Mitsunobu conditions furnished the linear heptadepsipeptide (XLVII). Removal of both Boc group and tert-butyl ester was accomplished by treatment with TFA at r.t. Finally, cyclization to the target compound was performed either with EDC and HOAt or with HATU and collidine.
| 【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XLIVI) | 26306 | (6S,9S,12S,15S)-6-isobutyl-9-[(1-methoxy-1H-indol-3-yl)methyl]-2,2,8,14,15-pentamethyl-12-[(2R)-2-methylhexyl]-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oic acid | C37H59N5O8 | 详情 | 详情 | |
| (XXXVIII) | 26299 | tert-butyl (2S)-2-[((2S,4R)-2-[[(2S)-4-cyano-2-hydroxybutanoyl]amino]-4-methyloctanoyl)(methyl)amino]-4-methylpentanoate | C25H45N3O5 | 详情 | 详情 | |
| (XLVII) | 26307 | tert-butyl (6S,9S,12S,15S,18R,21S,24S)-18-(2-cyanoethyl)-6,24-diisobutyl-9-[(1-methoxy-1H-indol-3-yl)methyl]-2,2,8,14,15,23-hexamethyl-12,21-bis[(2R)-2-methylhexyl]-4,7,10,13,16,19,22-heptaoxo-3,17-dioxa-5,8,11,14,20,23-hexaazapentacosan-25-oate | C62H102N8O12 | 详情 | 详情 |