用叠氮衍生物修饰 C6 位的 N-乙酰葡糖胺类似物的合成

Massimo Alagia, Lorenzo Taglietti, Barbara La Ferla
{"title":"用叠氮衍生物修饰 C6 位的 N-乙酰葡糖胺类似物的合成","authors":"Massimo Alagia, Lorenzo Taglietti, Barbara La Ferla","doi":"10.1007/s00706-024-03198-0","DOIUrl":null,"url":null,"abstract":"<p>We report a simple synthetic scheme for the preparation of several azido-derived analogues of <i>N</i>-acetylglucosamine (Glc<i>N</i>Ac). The synthesis of Glc<i>N</i>Ac analogues has been achieved through a straightforward approach starting from Glc<i>N</i>Ac-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 Glc<i>N</i>Ac-based drugs.</p><h3 data-test=\"abstract-sub-heading\">Graphical abstract</h3>\n","PeriodicalId":19011,"journal":{"name":"Monatshefte für Chemie / Chemical Monthly","volume":"3 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of N-acetylglucosamine analogues modified at C6 position with azido-derived moieties\",\"authors\":\"Massimo Alagia, Lorenzo Taglietti, Barbara La Ferla\",\"doi\":\"10.1007/s00706-024-03198-0\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>We report a simple synthetic scheme for the preparation of several azido-derived analogues of <i>N</i>-acetylglucosamine (Glc<i>N</i>Ac). The synthesis of Glc<i>N</i>Ac analogues has been achieved through a straightforward approach starting from Glc<i>N</i>Ac-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 Glc<i>N</i>Ac-based drugs.</p><h3 data-test=\\\"abstract-sub-heading\\\">Graphical abstract</h3>\\n\",\"PeriodicalId\":19011,\"journal\":{\"name\":\"Monatshefte für Chemie / Chemical Monthly\",\"volume\":\"3 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-03-25\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Monatshefte für Chemie / Chemical Monthly\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1007/s00706-024-03198-0\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte für Chemie / Chemical Monthly","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1007/s00706-024-03198-0","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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

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.

Graphical abstract

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
自引率
0.00%
发文量
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信