Selectivity in C-alkylation of dianions of protected 6-methyluridine
Identifieur interne : 000217 ( Ncbi/Merge ); précédent : 000216; suivant : 000218Selectivity 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.
Abstract
A regioselective synthesis of 6-ω-alkenyluridines
Url:
DOI: 10.3762/bjoc.7.143
PubMed: 21977207
PubMed Central: 3182432
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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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name><affiliation wicri:level="3"><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 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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><double pmid="21977207"><pmc><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">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="3"><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name><affiliation wicri:level="3"><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><placeName><region type="region" nuts="2">Hauts-de-France</region><region type="old region" nuts="2">Picardie</region><settlement type="city">Compiègne</settlement></placeName></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="3"><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name><affiliation 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organique moléculaire et macromoléculaire (UMR 6011), Faculté des sciences, avenue Olivier Messiaen, 72085 Le Mans Cedex 9</wicri:regionArea><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name><affiliation wicri:level="3"><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><placeName><region type="region" nuts="2">Hauts-de-France</region><region type="old region" nuts="2">Picardie</region><settlement type="city">Compiègne</settlement></placeName></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="3"><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name><affiliation wicri:level="3"><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author></analytic><series><title level="j">Beilstein Journal of Organic Chemistry</title><idno type="eISSN">1860-5397</idno><imprint><date when="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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><pubmed><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Selectivity in C-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="3"><nlm:affiliation>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:affiliation><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name></author><author><name sortKey="Castanet, Anne Sophie" sort="Castanet, Anne Sophie" uniqKey="Castanet A" first="Anne-Sophie" last="Castanet">Anne-Sophie Castanet</name></author><author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2011">2011</date><idno type="doi">10.3762/bjoc.7.143</idno><idno type="RBID">pubmed:21977207</idno><idno type="pmid">21977207</idno><idno type="wicri:Area/PubMed/Corpus">000095</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000095</idno><idno type="wicri:Area/PubMed/Curation">000095</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000095</idno><idno type="wicri:Area/PubMed/Checkpoint">000095</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000095</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Selectivity in C-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="3"><nlm:affiliation>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:affiliation><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><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Le Mans</settlement></placeName></affiliation></author><author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name></author><author><name sortKey="Castanet, Anne Sophie" sort="Castanet, Anne Sophie" uniqKey="Castanet A" first="Anne-Sophie" last="Castanet">Anne-Sophie Castanet</name></author><author><name sortKey="Mortier, Jacques" sort="Mortier, Jacques" uniqKey="Mortier J" first="Jacques" last="Mortier">Jacques Mortier</name></author></analytic><series><title level="j">Beilstein journal of organic chemistry</title><idno type="eISSN">1860-5397</idno><imprint><date when="2011" type="published">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">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.</div></front></TEI></pubmed></double></record>Pour manipuler ce document sous Unix (Dilib)
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