Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)

A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside β-ketophosphonate, readily available from the nucleobase and benzylacrylate, afforded a mixture of (R)- and (S)-β-hydroxyphosphonate derivatives which was resolved....

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Autores principales: Kasthuri, Mahesh, Chaloin, Laurent, Périgaud, Christian, Peyrottes, Suzanne
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125833/
https://www.ncbi.nlm.nih.gov/pubmed/32288328
http://dx.doi.org/10.1016/j.tetasy.2011.08.010
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author Kasthuri, Mahesh
Chaloin, Laurent
Périgaud, Christian
Peyrottes, Suzanne
author_facet Kasthuri, Mahesh
Chaloin, Laurent
Périgaud, Christian
Peyrottes, Suzanne
author_sort Kasthuri, Mahesh
collection PubMed
description A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside β-ketophosphonate, readily available from the nucleobase and benzylacrylate, afforded a mixture of (R)- and (S)-β-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies.
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spelling pubmed-71258332020-04-08 Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA) Kasthuri, Mahesh Chaloin, Laurent Périgaud, Christian Peyrottes, Suzanne Tetrahedron Asymmetry Article A synthetic pathway to new acyclonucleoside phosphonates, as analogues of Adefovir, is described. The reduction of an acyclonucleoside β-ketophosphonate, readily available from the nucleobase and benzylacrylate, afforded a mixture of (R)- and (S)-β-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies and was supported by molecular modelling studies. Elsevier Ltd. 2011-07-31 2011-10-01 /pmc/articles/PMC7125833/ /pubmed/32288328 http://dx.doi.org/10.1016/j.tetasy.2011.08.010 Text en Copyright © 2011 Elsevier Ltd. All rights reserved. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Kasthuri, Mahesh
Chaloin, Laurent
Périgaud, Christian
Peyrottes, Suzanne
Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title_full Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title_fullStr Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title_full_unstemmed Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title_short Synthesis of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides: structural analogues of Adefovir (PMEA)
title_sort synthesis of (r)- and (s)-β-hydroxyphosphonate acyclonucleosides: structural analogues of adefovir (pmea)
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7125833/
https://www.ncbi.nlm.nih.gov/pubmed/32288328
http://dx.doi.org/10.1016/j.tetasy.2011.08.010
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