【结 构 式】 |
【分子编号】58714 【品名】(2S)-4-(benzyloxy)-2-({(2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoyl}amino)-4-oxobutanoic acid 【CA登记号】 |
【 分 子 式 】C28H34N2O9 【 分 子 量 】542.58604 【元素组成】C 61.98% H 6.32% N 5.16% O 26.54% |
合成路线1
该中间体在本合成路线中的序号:(III)The title compound was obtained by solution-phase peptide synthesis. Acylation of L-aspartic acid beta-benzyl ester (II) with the succinimidyl ester of N-Boc-gamma-benzyl-L-glutamic acid (I) led to the protected dipeptide (III). Removal of the Boc protecting group of (III) by means of trifluoroacetic acid afforded amine (IV), which was subsequently condensed with N-Cbz-L-alanine succinimidyl ester (V) to furnish tripeptide (VI). Coupling of (VI) with glycine benzyl ester (VII) using DCC and HOBt gave the fully protected peptide (VIII). The N-Cbz and benzyl ester groups of (VIII) were finally removed by catalytic hydrogenation over Pd/C to provide the target tetrapeptide.
【1】 Khavinson, V.K.; Tetrapeptide revealing geroprotective effect, pharmacological substance on its basis, and the method of its application. WO 0068255 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 58712 | benzyl (4S)-4-[(tert-butoxycarbonyl)amino]-5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxopentanoate | C21H26N2O8 | 详情 | 详情 | |
(II) | 58713 | (2S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid | C11H13NO4 | 详情 | 详情 | |
(III) | 58714 | (2S)-4-(benzyloxy)-2-({(2S)-5-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-5-oxopentanoyl}amino)-4-oxobutanoic acid | C28H34N2O9 | 详情 | 详情 | |
(IV) | 58715 | (2S)-2-{[(2S)-2-amino-5-(benzyloxy)-5-oxopentanoyl]amino}-4-(benzyloxy)-4-oxobutanoic acid | C23H26N2O7 | 详情 | 详情 | |
(V) | 27317 | benzyl (1S)-2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1-methyl-2-oxoethylcarbamate | C15H16N2O6 | 详情 | 详情 | |
(VI) | 58716 | (5S,8S,11S)-11-[2-(benzyloxy)-2-oxoethyl]-8-[3-(benzyloxy)-3-oxopropyl]-5-methyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid | C34H37N3O10 | 详情 | 详情 | |
(VII) | 13601 | benzyl 2-aminoacetate; Glycine benzyl ester hydrochloride | 1738-68-7 | C9H11NO2 | 详情 | 详情 |
(VIII) | 58717 | benzyl (5S,8S,11S)-11-[2-(benzyloxy)-2-oxoethyl]-8-[3-(benzyloxy)-3-oxopropyl]-5-methyl-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oate | C43H46N4O11 | 详情 | 详情 |