Selectivity in C-alkylation of dianions of protected 6-methyluridine

A regioselective synthesis of 6-ω-alkenyluridines 3, precursors of potent antiviral and antitumor cyclonucleosides 5, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds 3 were prepared in a regioselective manner by sequential treatment of 6-methyluridine 2 with LTMP or...

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Autores principales: Nguyen, Ngoc Hoa, Len, Christophe, Castanet, Anne-Sophie, Mortier, Jacques
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182432/
https://www.ncbi.nlm.nih.gov/pubmed/21977207
http://dx.doi.org/10.3762/bjoc.7.143
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author Nguyen, Ngoc Hoa
Len, Christophe
Castanet, Anne-Sophie
Mortier, Jacques
author_facet Nguyen, Ngoc Hoa
Len, Christophe
Castanet, Anne-Sophie
Mortier, Jacques
author_sort Nguyen, Ngoc Hoa
collection PubMed
description A regioselective synthesis of 6-ω-alkenyluridines 3, precursors of potent antiviral and antitumor cyclonucleosides 5, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds 3 were prepared in a regioselective manner by sequential treatment of 6-methyluridine 2 with LTMP or LDA (4 equiv) in THF at −30 °C followed by alkylation with ω-alkenyl bromides.
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spelling pubmed-31824322011-10-05 Selectivity in C-alkylation of dianions of protected 6-methyluridine Nguyen, Ngoc Hoa Len, Christophe Castanet, Anne-Sophie Mortier, Jacques Beilstein J Org Chem Full Research Paper A regioselective synthesis of 6-ω-alkenyluridines 3, precursors of potent antiviral and antitumor cyclonucleosides 5, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds 3 were prepared in a regioselective manner by sequential treatment of 6-methyluridine 2 with LTMP or LDA (4 equiv) in THF at −30 °C followed by alkylation with ω-alkenyl bromides. Beilstein-Institut 2011-09-06 /pmc/articles/PMC3182432/ /pubmed/21977207 http://dx.doi.org/10.3762/bjoc.7.143 Text en Copyright © 2011, Nguyen et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Nguyen, Ngoc Hoa
Len, Christophe
Castanet, Anne-Sophie
Mortier, Jacques
Selectivity in C-alkylation of dianions of protected 6-methyluridine
title Selectivity in C-alkylation of dianions of protected 6-methyluridine
title_full Selectivity in C-alkylation of dianions of protected 6-methyluridine
title_fullStr Selectivity in C-alkylation of dianions of protected 6-methyluridine
title_full_unstemmed Selectivity in C-alkylation of dianions of protected 6-methyluridine
title_short Selectivity in C-alkylation of dianions of protected 6-methyluridine
title_sort selectivity in c-alkylation of dianions of protected 6-methyluridine
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182432/
https://www.ncbi.nlm.nih.gov/pubmed/21977207
http://dx.doi.org/10.3762/bjoc.7.143
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