AgOTf-catalyzed three-component coupling for the synthesis of C-alkynyl iminosugars

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-10-18 DOI:10.1016/j.tetlet.2024.155326

Goparaju Rakesh , V. Veerabhadra Reddy , Allam Vinaykumar , B.V. Subba Reddy

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.

Abstract Image

查看原文本刊更多论文

AgOTf 催化三组分偶联合成 C-炔基亚胺糖

在极其温和的条件下，使用一定量的 AgOTf 催化剂完成了对甲苯核糖、伯胺和炔的 A3 偶联，从而合成了 C-炔基亚胺糖。该反应通过环状亚氨基离子进行，亚氨基离子由甲苯基核糖和伯胺形成，然后与炔烃发生反应，形成 C-炔基亚氨基糖，它是许多重要生物天然产物的关键中间体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

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.