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【结 构 式】 
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【分子编号】62564 【品名】benzyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C26H38N2O6 【 分 子 量 】474.5976 【元素组成】C 65.8% H 8.07% N 5.9% O 20.23% |
合成路线1
该中间体在本合成路线中的序号：(XIX)Similarly, (S)-2-hydroxy-3-methylbutyric acid (LV) was protected as the silyl ether (LVI) and then condensed with benzyl acetate, via activation with CDI, to afford keto ester (LVII). Subsequent methylation of (LVII) using iodomethane and NaH provided (XVI) as a diastereomeric mixture. The unstable keto acid (XVII), obtained in situ by catalytic hydrogenolysis of (XVI), was then coupled to the dipeptide ester (XV) to afford, after desilylation, the hydroxy keto amide (XIX). Esterification of alcohol (XIX) with the isostatine derivative (XI) as in Scheme 3, followed by acidic cleavage of the O-silyl and N-Boc protecting groups led to depsipeptide (XXI)
| 【1】 Edge, A. (Diacrin, Inc.); Method for improving graft acceptance in a recipient by administration of a cytokine profile altering agent. WO 0051630 . |
| 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) | 50802 | (3S,4R,5S)-4-[(tert-butoxycarbonyl)amino]-3-[[tert-butyl(dimethyl)silyl]oxy]-5-methylheptanoic acid | C19H39NO5Si | 详情 | 详情 | |
| (XV) | 50792 | benzyl (2S)-1-[(2S)-2-amino-4-methylpentanoyl]-2-pyrrolidinecarboxylate | C18H26N2O3 | 详情 | 详情 | |
| (XVI) | 62563 | benzyl (4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2,5-dimethyl-3-oxohexanoate | C21H34O4Si | 详情 | 详情 | |
| (XVII) | 50791 | (2S,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2,5-dimethyl-3-oxohexanoic acid | C14H28O4Si | 详情 | 详情 | |
| (XIX) | 62564 | benzyl (2S)-1-((2S)-2-{[(4S)-4-hydroxy-2,5-dimethyl-3-oxohexanoyl]amino}-4-methylpentanoyl)-2-pyrrolidinecarboxylate | C26H38N2O6 | 详情 | 详情 | |
| (XXI) | 62536 | benzyl (2S)-1-{(2S)-2-[((4S)-4-{[(3S,4R,5S)-4-amino-3-hydroxy-5-methylheptanoyl]oxy}-2,5-dimethyl-3-oxohexanoyl)amino]-4-methylpentanoyl}-2-pyrrolidinecarboxylate | C34H53N3O8 | 详情 | 详情 | |
| (LV) | 37829 | (2S)-2-hydroxy-3-methylbutyric acid | C5H10O3 | 详情 | 详情 | |
| (LVI) | 52726 | (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutanoic acid | C11H24O3Si | 详情 | 详情 | |
| (LVII) | 50790 | benzyl (4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-3-oxohexanoate | C20H32O4Si | 详情 | 详情 |