Investigations to mechanism and applications of the glycosylation protocol employing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycoside donors

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2022-01-01 DOI:10.1080/07328303.2022.2045021

Si-Yu Zhou , Hui-Juan Liu , Qing-Ju Zhang , Jin-Xi Liao , De-Yong Liu , Ming-Dong Li , Jian-Song Sun

引用次数: 1

Abstract

Based on the capability of silyl ethers for efficient glycosylation, the new MTEAN glycosylation protocol utilizing 8-methyltosylaminoethynyl-1-naphthyl (MTEAN) glycosides as donors were extended to one-pot synthesis of nucleosides, late-stage modification of bioactive molecules, and stereoselective construction of 1,2-cis-glucosidic linkages using silyl ethers of the acceptors. Moreover, the reaction mechanism was systematically investigated by control reactions and side product characterizations, leading to the determination of a TfOH-catalyzed ynamide functionality-initiated process, which was further corroborated by identifications of the departure form of leaving group and the real catalyst.

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8-甲基甲酰基氨基乙基-1-萘基(MTEAN)糖苷供体糖基化机制及应用研究

基于硅基醚高效糖基化的能力，新的MTEAN糖基化方案利用8-甲基甲酰基氨基乙基-1-萘基(MTEAN)糖苷作为供体扩展到核苷的一锅合成，生物活性分子的后期修饰，以及利用受体的硅基醚立体选择性构建1,2-顺式糖苷键。此外，通过对照反应和副产物表征对反应机理进行了系统研究，确定了tfoh催化的酰胺官能团引发反应过程，并通过对离去基的离去形式和真实催化剂的鉴定进一步证实了这一结论。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.