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

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

Auteurs : Ngoc Hoa Nguyen [France] ; Christophe Len [France] ; Anne-Sophie Castanet [France] ; Jacques Mortier [France]

Source :

Beilstein Journal of Organic Chemistry [ 1860-5397 ] ; 2011.

RBID : PMC:3182432

Abstract

Summary

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.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3182432

DOI: 10.3762/bjoc.7.143
PubMed: 21977207
PubMed Central: 3182432

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Le document en format XML

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-alkylation of dianions of protected 6-methyluridine</title>
<author><name sortKey="Nguyen, Ngoc Hoa" sort="Nguyen, Ngoc Hoa" uniqKey="Nguyen N" first="Ngoc Hoa" last="Nguyen">Ngoc Hoa Nguyen</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea>
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<author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name>
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<country xml:lang="fr">France</country>
<wicri:regionArea>Université de technologie de Compiègne, Transformations intégrées de la matière renouvelable, EA 4297 UTC/ESCOM, 1 allée du réseau Jean-Marie Buckmaster, 60200 Compiègne</wicri:regionArea>
</affiliation>
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<author><name sortKey="Castanet, Anne Sophie" sort="Castanet, Anne Sophie" uniqKey="Castanet A" first="Anne-Sophie" last="Castanet">Anne-Sophie Castanet</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea>
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<author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Selectivity in <italic>C</italic>
-alkylation of dianions of protected 6-methyluridine</title>
<author><name sortKey="Nguyen, Ngoc Hoa" sort="Nguyen, Ngoc Hoa" uniqKey="Nguyen N" first="Ngoc Hoa" last="Nguyen">Ngoc Hoa Nguyen</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea>
</affiliation>
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<author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name>
<affiliation wicri:level="1"><nlm:aff id="A2">Université de technologie de Compiègne, Transformations intégrées de la matière renouvelable, EA 4297 UTC/ESCOM, 1 allée du réseau Jean-Marie Buckmaster, 60200 Compiègne, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université de technologie de Compiègne, Transformations intégrées de la matière renouvelable, EA 4297 UTC/ESCOM, 1 allée du réseau Jean-Marie Buckmaster, 60200 Compiègne</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Castanet, Anne Sophie" sort="Castanet, Anne Sophie" uniqKey="Castanet A" first="Anne-Sophie" last="Castanet">Anne-Sophie Castanet</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea>
</affiliation>
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<author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name>
<affiliation wicri:level="1"><nlm:aff id="A1">Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea>
</affiliation>
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<series><title level="j">Beilstein Journal of Organic Chemistry</title>
<idno type="eISSN">1860-5397</idno>
<imprint><date when="2011">2011</date>
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<front><div type="abstract" xml:lang="en"><title>Summary</title>
<p>A regioselective synthesis of 6-ω-alkenyluridines <bold>3</bold>
, precursors of potent antiviral and antitumor cyclonucleosides <bold>5</bold>
, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds <bold>3</bold>
 were prepared in a regioselective manner by sequential treatment of 6-methyluridine <bold>2</bold>
 with LTMP or LDA (4 equiv) in THF at −30 °C followed by alkylation with ω-alkenyl bromides.</p>
</div>
</front>
</TEI>
<pmc article-type="research-article"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Beilstein J Org Chem</journal-id>
<journal-title-group><journal-title>Beilstein Journal of Organic Chemistry</journal-title>
</journal-title-group>
<issn pub-type="epub">1860-5397</issn>
<publisher><publisher-name>Beilstein-Institut</publisher-name>
<publisher-loc>Trakehner Str. 7-9, 60487 Frankfurt am Main, Germany</publisher-loc>
</publisher>
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<article-meta><article-id pub-id-type="pmid">21977207</article-id>
<article-id pub-id-type="pmc">3182432</article-id>
<article-id pub-id-type="doi">10.3762/bjoc.7.143</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Full Research Paper</subject>
</subj-group>
<subj-group subj-group-type="topic"><subject>Chemistry</subject>
<subj-group subj-group-type="topic"><subject>Organic Chemistry</subject>
</subj-group>
</subj-group>
</article-categories>
<title-group><article-title>Selectivity in <italic>C</italic>
-alkylation of dianions of protected 6-methyluridine</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Nguyen</surname>
<given-names>Ngoc Hoa</given-names>
</name>
<email>bexiuhn@yahoo.com</email>
<xref ref-type="aff" rid="A1">1</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Len</surname>
<given-names>Christophe</given-names>
</name>
<email>christophe.len@utc.fr</email>
<xref ref-type="aff" rid="A2">2</xref>
</contrib>
<contrib contrib-type="author" corresp="yes"><name><surname>Castanet</surname>
<given-names>Anne-Sophie</given-names>
</name>
<email>anne-sophie.castanet@univ-lemans.fr</email>
<xref ref-type="aff" rid="A1">1</xref>
</contrib>
<contrib contrib-type="author" corresp="yes"><name><surname>Mortier</surname>
<given-names>Jacques</given-names>
</name>
<email>jacques.mortier@univ-lemans.fr</email>
<xref ref-type="aff" rid="A1">1</xref>
<xref ref-type="author-notes" rid="FN1">§</xref>
</contrib>
</contrib-group>
<contrib-group><contrib contrib-type="editor"><name><surname>Snieckus</surname>
<given-names>Victor</given-names>
</name>
<role>Guest Editor</role>
</contrib>
</contrib-group>
<aff id="A1"><label>1</label>
Université du Maine and CNRS, Unité de chimie organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France</aff>
<aff id="A2"><label>2</label>
Université de technologie de Compiègne, Transformations intégrées de la matière renouvelable, EA 4297 UTC/ESCOM, 1 allée du réseau Jean-Marie Buckmaster, 60200 Compiègne, France</aff>
<author-notes><fn id="FN1"><label>§</label>
<p>Fax: +33 (0) 243 83 39 02</p>
</fn>
</author-notes>
<pub-date pub-type="collection"><year>2011</year>
</pub-date>
<pub-date pub-type="epub"><day>6</day>
<month>9</month>
<year>2011</year>
</pub-date>
<volume>7</volume>
<fpage>1228</fpage>
<lpage>1233</lpage>
<ext-link ext-link-type="doi" xlink:href="10.3762/bjoc.7.143">10.3762/bjoc.7.143</ext-link>
<history><date date-type="received"><day>22</day>
<month>3</month>
<year>2011</year>
</date>
<date date-type="accepted"><day>16</day>
<month>6</month>
<year>2011</year>
</date>
</history>
<permissions><copyright-statement>Copyright © 2011, Nguyen et al; licensee Beilstein-Institut.</copyright-statement>
<copyright-year>2011</copyright-year>
<copyright-holder>Nguyen et al; licensee Beilstein-Institut.</copyright-holder>
<license license-type="Beilstein" xlink:href="http://www.beilstein-journals.org/bjoc"><license-p>This is an Open Access article under the terms of the Creative Commons Attribution License (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/2.0">http://creativecommons.org/licenses/by/2.0</ext-link>
), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.</license-p>
<license-p>The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (<ext-link ext-link-type="uri" xlink:href="http://www.beilstein-journals.org/bjoc">http://www.beilstein-journals.org/bjoc</ext-link>
)</license-p>
</license>
</permissions>
<abstract><title>Summary</title>
<p>A regioselective synthesis of 6-ω-alkenyluridines <bold>3</bold>
, precursors of potent antiviral and antitumor cyclonucleosides <bold>5</bold>
, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds <bold>3</bold>
 were prepared in a regioselective manner by sequential treatment of 6-methyluridine <bold>2</bold>
 with LTMP or LDA (4 equiv) in THF at −30 °C followed by alkylation with ω-alkenyl bromides.</p>
</abstract>
<abstract abstract-type="graphical"><p><disp-formula id="graphical-abstract"><graphic xlink:href="Beilstein_J_Org_Chem-07-1228-g001"></graphic>
</disp-formula>
</p>
</abstract>
<kwd-group kwd-group-type="author"><kwd>C6-alkylation</kwd>
<kwd>cyclonucleosides</kwd>
<kwd>lithiations</kwd>
<kwd>6-ω-alkenyluridines</kwd>
</kwd-group>
</article-meta>
<notes><p>This article is part of the Thematic Series "Directed aromatic functionalization"</p>
</notes>
</front>
</pmc>
</record>

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

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

Source :

Abstract

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