Issue 3, 2025

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
05 ноя 2024
Accepted
20 ноя 2024
First published
21 ноя 2024

Org. Biomol. Chem., 2025,23, 579-588

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

N. Sakander and Q. N. Ahmed, Org. Biomol. Chem., 2025, 23, 579 DOI: 10.1039/D4OB01788A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements