Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
Identifieur interne : 000324 ( Istex/Corpus ); précédent : 000323; suivant : 000325Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
Auteurs : Hiromichi Tanaka ; Hiroyuki Hayakawa ; Kikoh Obi ; Miyasaka TadashiSource :
- Tetrahedron [ 0040-4020 ] ; 1986.
English descriptors
- KwdEn :
- Anal, Benzene, Calcd, Cdcl, Chcl, Chem, Column chromatography, Derivative, Desulfurizative, Desulfurizative stannylation, Deuteration, Equiv, Etoh, Hayakawa, Ltmp, Meoh, Miyasaka, Mmol, Phenylthio group, Physical data, Reagent, Room temperature, Silica, Stannylation, Tanaka, Tbth, Tetrahedron, Tetrahedron lett.
- Teeft :
- Anal, Benzene, Calcd, Cdcl, Chcl, Chem, Column chromatography, Derivative, Desulfurizative, Desulfurizative stannylation, Deuteration, Equiv, Etoh, Hayakawa, Ltmp, Meoh, Miyasaka, Mmol, Phenylthio group, Physical data, Reagent, Room temperature, Silica, Stannylation, Tanaka, Tbth, Tetrahedron, Tetrahedron lett.
Abstract
Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.
Url:
DOI: 10.1016/S0040-4020(01)87642-0
Links to Exploration step
ISTEX:051FC5FB9D9C64E6DEC29BF826A32A92496829CCLe document en format XML
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University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author><author><name sortKey="Tadashi, Miyasaka" sort="Tadashi, Miyasaka" uniqKey="Tadashi M" first="Miyasaka" last="Tadashi">Miyasaka Tadashi</name><affiliation><mods:affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:051FC5FB9D9C64E6DEC29BF826A32A92496829CC</idno><date when="1986" year="1986">1986</date><idno type="doi">10.1016/S0040-4020(01)87642-0</idno><idno type="url">https://api.istex.fr/document/051FC5FB9D9C64E6DEC29BF826A32A92496829CC/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">000324</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000324</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a">Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title><author><name sortKey="Tanaka, Hiromichi" sort="Tanaka, Hiromichi" uniqKey="Tanaka H" first="Hiromichi" last="Tanaka">Hiromichi Tanaka</name><affiliation><mods:affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author><author><name sortKey="Hayakawa, Hiroyuki" sort="Hayakawa, Hiroyuki" uniqKey="Hayakawa H" first="Hiroyuki" last="Hayakawa">Hiroyuki Hayakawa</name><affiliation><mods:affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author><author><name sortKey="Obi, Kikoh" sort="Obi, Kikoh" uniqKey="Obi K" first="Kikoh" last="Obi">Kikoh Obi</name><affiliation><mods:affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author><author><name sortKey="Tadashi, Miyasaka" sort="Tadashi, Miyasaka" uniqKey="Tadashi M" first="Miyasaka" last="Tadashi">Miyasaka Tadashi</name><affiliation><mods:affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="ISSN">0040-4020</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1986">1986</date><biblScope unit="volume">42</biblScope><biblScope unit="issue">15</biblScope><biblScope unit="page" from="4187">4187</biblScope><biblScope unit="page" to="4195">4195</biblScope></imprint><idno type="ISSN">0040-4020</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4020</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Anal</term><term>Benzene</term><term>Calcd</term><term>Cdcl</term><term>Chcl</term><term>Chem</term><term>Column chromatography</term><term>Derivative</term><term>Desulfurizative</term><term>Desulfurizative stannylation</term><term>Deuteration</term><term>Equiv</term><term>Etoh</term><term>Hayakawa</term><term>Ltmp</term><term>Meoh</term><term>Miyasaka</term><term>Mmol</term><term>Phenylthio group</term><term>Physical data</term><term>Reagent</term><term>Room temperature</term><term>Silica</term><term>Stannylation</term><term>Tanaka</term><term>Tbth</term><term>Tetrahedron</term><term>Tetrahedron lett</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Anal</term><term>Benzene</term><term>Calcd</term><term>Cdcl</term><term>Chcl</term><term>Chem</term><term>Column chromatography</term><term>Derivative</term><term>Desulfurizative</term><term>Desulfurizative stannylation</term><term>Deuteration</term><term>Equiv</term><term>Etoh</term><term>Hayakawa</term><term>Ltmp</term><term>Meoh</term><term>Miyasaka</term><term>Mmol</term><term>Phenylthio group</term><term>Physical data</term><term>Reagent</term><term>Room temperature</term><term>Silica</term><term>Stannylation</term><term>Tanaka</term><term>Tbth</term><term>Tetrahedron</term><term>Tetrahedron lett</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</div></front></TEI><istex><corpusName>elsevier</corpusName><keywords><teeft><json:string>mmol</json:string><json:string>tbth</json:string><json:string>meoh</json:string><json:string>chem</json:string><json:string>cdcl</json:string><json:string>ltmp</json:string><json:string>calcd</json:string><json:string>column chromatography</json:string><json:string>chcl</json:string><json:string>deuteration</json:string><json:string>etoh</json:string><json:string>equiv</json:string><json:string>tetrahedron</json:string><json:string>miyasaka</json:string><json:string>tanaka</json:string><json:string>desulfurizative</json:string><json:string>anal</json:string><json:string>hayakawa</json:string><json:string>stannylation</json:string><json:string>room temperature</json:string><json:string>derivative</json:string><json:string>desulfurizative stannylation</json:string><json:string>silica</json:string><json:string>reagent</json:string><json:string>physical data</json:string><json:string>phenylthio group</json:string><json:string>tetrahedron lett</json:string><json:string>benzene</json:string></teeft></keywords><author><json:item><name>Hiromichi Tanaka</name><affiliations><json:string>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</json:string></affiliations></json:item><json:item><name>Hiroyuki Hayakawa</name><affiliations><json:string>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</json:string></affiliations></json:item><json:item><name>Kikoh Obi</name><affiliations><json:string>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</json:string></affiliations></json:item><json:item><name>Miyasaka Tadashi</name><affiliations><json:string>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</json:string></affiliations></json:item></author><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><abstract>phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</abstract><qualityIndicators><score>4.331</score><pdfVersion>1.2</pdfVersion><pdfPageSize>468 x 754 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>586</abstractCharCount><pdfWordCount>3383</pdfWordCount><pdfCharCount>27095</pdfCharCount><pdfPageCount>9</pdfPageCount><abstractWordCount>79</abstractWordCount></qualityIndicators><title>Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title><pii><json:string>S0040-4020(01)87642-0</json:string></pii><genre><json:string>research-article</json:string></genre><host><title>Tetrahedron</title><language><json:string>unknown</json:string></language><publicationDate>1986</publicationDate><issn><json:string>0040-4020</json:string></issn><pii><json:string>S0040-4020(00)X0504-2</json:string></pii><volume>42</volume><issue>15</issue><pages><first>4187</first><last>4195</last></pages><genre><json:string>journal</json:string></genre></host><categories><wos><json:string>science</json:string><json:string>chemistry, organic</json:string></wos><scienceMetrix><json:string>natural sciences</json:string><json:string>chemistry</json:string><json:string>organic chemistry</json:string></scienceMetrix><inist><json:string>sciences appliquees, technologies et medecines</json:string><json:string>sciences biologiques et medicales</json:string><json:string>sciences medicales</json:string><json:string>toxicologie</json:string></inist></categories><publicationDate>1986</publicationDate><copyrightDate>1986</copyrightDate><doi><json:string>10.1016/S0040-4020(01)87642-0</json:string></doi><id>051FC5FB9D9C64E6DEC29BF826A32A92496829CC</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/051FC5FB9D9C64E6DEC29BF826A32A92496829CC/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/051FC5FB9D9C64E6DEC29BF826A32A92496829CC/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/051FC5FB9D9C64E6DEC29BF826A32A92496829CC/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>ELSEVIER</p></availability><date>1986</date></publicationStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a">Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title><author xml:id="author-0000"><persName><forename type="first">Hiromichi</forename><surname>Tanaka</surname></persName><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation></author><author xml:id="author-0001"><persName><forename type="first">Hiroyuki</forename><surname>Hayakawa</surname></persName><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation></author><author xml:id="author-0002"><persName><forename type="first">Kikoh</forename><surname>Obi</surname></persName><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation></author><author xml:id="author-0003"><persName><forename type="first">Miyasaka</forename><surname>Tadashi</surname></persName><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation></author><idno type="istex">051FC5FB9D9C64E6DEC29BF826A32A92496829CC</idno><idno type="DOI">10.1016/S0040-4020(01)87642-0</idno><idno type="PII">S0040-4020(01)87642-0</idno></analytic><monogr><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="pISSN">0040-4020</idno><idno type="PII">S0040-4020(00)X0504-2</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1986"></date><biblScope unit="volume">42</biblScope><biblScope unit="issue">15</biblScope><biblScope unit="page" from="4187">4187</biblScope><biblScope unit="page" to="4195">4195</biblScope></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1986</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</p></abstract></profileDesc><revisionDesc><change when="1986">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/051FC5FB9D9C64E6DEC29BF826A32A92496829CC/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla"><item-info><jid>TET</jid><aid>01876420</aid><ce:pii>S0040-4020(01)87642-0</ce:pii><ce:doi>10.1016/S0040-4020(01)87642-0</ce:doi><ce:copyright type="unknown" year="1986"></ce:copyright></item-info><head><ce:title>Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</ce:title><ce:author-group><ce:author><ce:given-name>Hiromichi</ce:given-name><ce:surname>Tanaka</ce:surname></ce:author><ce:author><ce:given-name>Hiroyuki</ce:given-name><ce:surname>Hayakawa</ce:surname></ce:author><ce:author><ce:given-name>Kikoh</ce:given-name><ce:surname>Obi</ce:surname></ce:author><ce:author><ce:surname>Tadashi</ce:surname><ce:given-name>Miyasaka</ce:given-name><ce:ranking><ce:sup>∗</ce:sup></ce:ranking></ce:author><ce:affiliation><ce:textfn>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</ce:textfn></ce:affiliation></ce:author-group><ce:date-received day="30" month="4" year="1986"></ce:date-received><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.</ce:simple-para></ce:abstract-sec></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation</title></titleInfo><name type="personal"><namePart type="given">Hiromichi</namePart><namePart type="family">Tanaka</namePart><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Hiroyuki</namePart><namePart type="family">Hayakawa</namePart><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Kikoh</namePart><namePart type="family">Obi</namePart><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Miyasaka</namePart><namePart type="family">Tadashi</namePart><affiliation>School of Pharmaceutical Sciences, Showa University,Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142, Japan</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-1JC4F85T-7">research-article</genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1986</dateIssued><copyrightDate encoding="w3cdtf">1986</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><abstract lang="en">Abstract: phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. 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