Stereoselective synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides: solvent-free Lewis acid catalysis.

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-11-27 DOI:10.1039/d4ob01788a

Norein Sakander, Qazi Naveed Ahmed

引用次数: 0

Abstract

An expedient solvent-free synthesis of 2-deoxy-2-bromo-hexopyrano-β-nucleosides stereo- and regioselectively from protected glycals and unactivated nucleobases using cheaper and easily available reagent systems has been developed. The synthesis is mediated by a Lewis acid and is solvent-free. The substrate scope of the reaction was analysed with ether, ester and silyl-protected glycals as donors and different pyrimidine and purine bases were taken into consideration. This method further finds application in the synthesis of 2-deoxynucleosides.

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2-deoxy-2-bromo-hexopyrano-β-nucleosides 的立体选择性合成：无溶剂路易斯酸催化。

本研究开发了一种便捷的无溶剂合成方法，可利用较便宜且易于获得的试剂体系，从受保护的甘氨酸和未活化的核碱基中立体选择性和区域选择性地合成 2-脱氧-2-溴-己吡喃-β-核苷。该合成由路易斯酸介导，无溶剂。以醚、酯和硅烷保护的甘氨酸为供体，分析了反应的底物范围，并考虑了不同的嘧啶和嘌呤碱基。该方法还可用于合成 2-脱氧核苷。

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

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.