{"title":"AgOTf-catalyzed three-component coupling for the synthesis of C-alkynyl iminosugars","authors":"Goparaju Rakesh , V. Veerabhadra Reddy , Allam Vinaykumar , B.V. Subba Reddy","doi":"10.1016/j.tetlet.2024.155326","DOIUrl":null,"url":null,"abstract":"<div><div>A<sup>3</sup> coupling of tosylribose, primary amine and alkyne has been accomplished for the synthesis of <em>C</em>-alkynyl iminosugars using a catalytic amount of AgOTf under extremely mild conditions. This method is compatible with acid sensitive acetonide and cyclohexylidene and also TBS and PMB ethers The reaction proceeds through a cyclic iminium ion, which is formed from tosylribose and a primary amine followed by the attack of alkyne resulting in the formation of <em>C</em>-alkynyl iminosugar, which is a key intermediate of many biologically important natural products.</div></div>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004210","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A3 coupling of tosylribose, primary amine and alkyne has been accomplished for the synthesis of C-alkynyl iminosugars using a catalytic amount of AgOTf under extremely mild conditions. This method is compatible with acid sensitive acetonide and cyclohexylidene and also TBS and PMB ethers The reaction proceeds through a cyclic iminium ion, which is formed from tosylribose and a primary amine followed by the attack of alkyne resulting in the formation of C-alkynyl iminosugar, which is a key intermediate of many biologically important natural products.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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