| N-叔丁氧羰基-DL-(±)-高酪氨酸的合成 |
| 投稿时间：2010-05-02 修订日期：2010-05-27 点此下载全文 |
| 引用本文：刘红明,秦烨,姚建忠,盛春泉,缪震元,张万年.N-叔丁氧羰基-DL-(±)-高酪氨酸的合成[J].药学实践杂志,2010,28(5):345~347,384 |
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| 基金项目:国家自然科学基金(30772674、30930107);上海市重点学科建设基金(B906)资助项目 |
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| 中文摘要:目的:制备用于新型多肽类药物全合成研究的非必需氨基酸N-叔丁氧羰基-DL-(±)-高酪氨酸(1)。方法:以L-天冬氨酸(2)为原料,经N-甲氧羰基保护、分子内脱水酸酐化、与邻氯苯甲醚的Friedel-Crafts反应、10%钯碳催化氢化、48%氢溴酸脱N-甲氧羰基和酚甲醚保护、N-叔丁氧羰基保护6步反应合成了目标化合物。结果:以总收率49.7%成功地合成了目标化合物1,其结构经电喷雾质谱(ESI-MS)、氢谱(1H NMR)和碳谱(13C NMR)确认。结论:该合成路线具有原料价廉易得、操作简便、总收率高等优点。 |
| 中文关键词:N-叔丁氧羰基-DL-(±)-高酪氨酸 合成 L-天冬氨酸 Friedel-Crafts反应 催化氢化 |
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| Synthesis of N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine |
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| Abstract:Objective To prepare N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine(1),a key unusual amino acid and pharmaceutical intermediate for the total synthesis of novel peptides drug including cyclic or straight chain peptide.Methods Starting from L-aspartic acid(2),the target compound 1 was synthesized via 6 steps including N-methoxycarbonylation,intramolecular dehydration and anhydridation,Friedel-Crafts reaction with 2-chloroanisole,catalytic hydrogenation with 10% Pd-C,N-demethoxycarbonylation and demethylation with 48% HBr-HOAc followed by N-Butoxycarbonylation.Results Target compound 1 had been successfully synthesized in an overall yield of 49.7%.The structure of the target compound was confirmed by ESI-MS,1H NMR and 1C NMR.Conclusion The process developed has several advantages such as cheap materials,convenient workup and high yield. |
| keywords:N-tert-butoxycarbonyl-DL-(±)-homo-tyrosine synthesis L-aspartic acid Friedel-Crafts reaction catalytic hydrogenation |
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