Massimo Alagia, Lorenzo Taglietti, Barbara La Ferla
{"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}
引用次数: 0
Abstract
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.
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