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Synthesis of Isonitrile Derivatives of Diglycerides and Carbohydrates as Intermediates for Multicomponent Ugi Reaction
Russian Journal of Bioorganic Chemistry ( IF 1 ) Pub Date : 2021-08-21 , DOI: 10.1134/s1068162021040166
A. I. Nichugovskiy 1 , A. A. Khrulev 1 , K. A. Perevoshchikova 1 , N. G. Morozova 1 , M. A. Maslov 1 , D. A. Cheshkov 2
Affiliation  

Abstract

Recently, there has been an increase in interest in multicomponent reactions, mainly due to the possibility of assembling of complex organic molecules in just several steps. Isocyanide is a key reagent for the Ugi multicomponent reaction. Isocyanide exhibits dual properties both electrophilic and nucleophilic. Several ways of formation of isonitrile derivatives are known, but the intramolecular dehydration of formamide is considered to be the main method. In this study, we synthesized isonitrile derivatives of dialkyl glycerol and D-glucose which can serve as new useful blocks for the creation of chemical libraries of lipophilic amines with the carbohydrate residue at their terminal nitrogen atom during the further interaction under the conditions of the multicomponent reactions. Structures of all the synthesized compounds were confirmed by physicochemical analytical methods, and these compounds can be used as blocks for the Ugi multicomponent reaction.



中文翻译:

作为多组分 Ugi 反应中间体的甘油二酯和碳水化合物异腈衍生物的合成

摘要

最近,人们对多组分反应的兴趣有所增加,这主要是由于只需几个步骤即可组装复杂的有机分子。异氰化物是 Ugi 多组分反应的关键试剂。异氰化物具有亲电和亲核双重特性。异腈衍生物的几种形成方式是已知的,但甲酰胺的分子内脱水被认为是主要的方法。在这项研究中,我们合成了二烷基甘油和 D-葡萄糖的异腈衍生物,它们可以作为新的有用嵌段,用于在多组分条件下的进一步相互作用过程中创建具有末端氮原子上的碳水化合物残基的亲脂胺化学库。反应。

更新日期:2021-08-21
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