用叠氮衍生物修饰 C6 位的 N-乙酰葡糖胺类似物的合成

Monatshefte für Chemie / Chemical Monthly Pub Date : 2024-03-25 DOI:10.1007/s00706-024-03198-0

Massimo Alagia, Lorenzo Taglietti, Barbara La Ferla

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摘要

我们报告了一种制备 N-乙酰葡糖胺（GlcNAc）的几种叠氮衍生物类似物的简单合成方案。GlcNAc 类似物的合成是以 GlcNAc-OMe 为起点，通过中间 C6 叠氮衍生物直接合成的。然后，通过叠氮-炔烃环加成反应和同一叠氮中间体的还原衍生反应，分别获得了本研究报告中的产品。这一合成途径提供了不同的功能化可能性，可用于制备新型 GlcNAc 基药物。

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Synthesis of N-acetylglucosamine analogues modified at C6 position with azido-derived moieties

We report a simple synthetic scheme for the preparation of several azido-derived analogues of N-acetylglucosamine (GlcNAc). The synthesis of GlcNAc analogues has been achieved through a straightforward approach starting from GlcNAc-OMe via an intermediate C6 azido derivative. Products reported in this work were then obtained respectively by azido-alkyne cycloaddition reactions and reductive derivatizations of the same azido-intermediate. This synthetic pathway presents different possibilities of functionalization that can be exploited for the preparation of novel GlcNAc-based drugs.