L-5-羟基色氨酸衍生物的合成  

Synthesis of L-5-Hydroxytryptophan Derivatives

作　　者：秦子康 郭海慧 单方 吴磊 王福生 Qin Zikang;Guo Haihui;Shan Fang;Wu Lei;Wang Fusheng(College of Pharmacy,Dali University,Dali,Yunnan 671000,China)

机构地区：[1]大理大学药学院,云南大理671000

出　　处：《大理大学学报》2023年第8期15-20,共6页Journal of Dali University

基　　金：国家自然科学基金项目(82260679);云南省地方本科高校基础研究联合专项资金项目(2019FH001-002)。

摘　　要：目的:拓宽色氨酸衍生物的类别,以便合成单萜吲哚生物碱。方法:以商业易得的L-5-羟基色氨酸为原料,经羧基酯化、氨基Boc保护、酯的氨解、羟基的乙酰化或甲基化反应以及脱Boc保护等反应步骤合成L-5-羟基色氨酸衍生物。结果:高效合成了7个L-5-羟基色氨酸衍生物,分别为L-5-羟基色氨酸甲酰胺(1)、L-5-羟基色氨酸乙酰胺(2)、L-5-羟基色氨酸丙酰胺(3)、L-5-乙酰氧基色氨酸甲酯(4)、L-5-乙酰氧基色氨酸甲酰胺(5)、L-5-甲氧基色氨酸甲酯(6)和L-5-甲氧基色氨酸甲酰胺(7)。化合物4、5和7为新衍生物,所有衍生物的结构经波谱学方法确证。结论:该合成方法具有操作简单、反应条件温和、总收率高的特点,适用于工业化生产。Objective:To broaden the categories of tryptophan derivatives for the synthesis of monothylindole alkaloids.Methods:Using commercially available L-5-hydroxytryptophan as raw material,L-5-hydroxytryptophan derivatives were synthesized through carboxyl esterification,amino Boc protection,ester ammonolysis,acetylation or methylation of hydroxyl and deprotection of Boc.Results:Secen L-5-hydroxytryptophan derivatives were efficiently synthesized,namely L-5-hydroxytryptophan formamide(1),L-5-hydroxytryptophan acetamide(2),L-5-hydroxytryptophan propionamide(3),L-5-acetoxytryptophan methyl ester(4),L-5-acetoxytryptophan formamide(5),L-5-methoxytryptophan methyl ester(6)and L-5-methoxytryptophan formamide(7),respectively.Compounds 4,5 and 7 were new derivatives,and the structures of all derivatives were confirmed by spectroscopic methods.Conclusion:The synthesis method has the characteristics of simple operation,mild reaction condition and high total yield,which is suitable for industrial production.

关 键 词：酯的氨解 乙酰化反应 甲基化反应 L-5-羟基色氨酸衍生物 合成 

分 类 号：TQ463[化学工程—制药化工]