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Current Medicinal Chemistry

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Review Article

Recent Advances in the Synthesis of 5′-deoxynucleoside Phosphonate Analogs

Author(s): Guang Huan Shen and Joon Hee Hong*

Volume 29, Issue 22, 2022

Published on: 17 January, 2022

Page: [3857 - 3921] Pages: 65

DOI: 10.2174/0929867328666211111162447

Price: $65

Abstract

The present review focuses on the synthesis of cyclic 5′-deoxynucleoside phosphonate analogs. The formation of various phosphonate alkyl moieties is accomplished through (i) Wittig (or HWE) type condensation to the nucleoside aldehyde moiety; (ii) nucleophilic displacement reaction using phosphonate anion or Lewis acid; (iii) Arbuzov reaction; (iv) olefin cross-metathesis between vinyl phosphonates and vinylated nucleosides; and (v) radical reaction and Pd catalyzed alkyne. For the coupling of nucleobases with cyclic moieties, the Mitsunobu reaction and Sonogashira-type cross-coupling are usually applied. For the coupling of furanose moieties with nucleobases, Vorbrüggentype condensation is generally applied. Addition reactions mediated by selenium ions are mainly applied for the coupling of carbocyclic moieties. Their biological activity results have been summarized.

Keywords: 5′-Deoxynucleoside phosphonates, antiviral agents, enzyme inhibitors, bioisostere, nucleoside, nucleoside- mimicking analogs.

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