Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)
Identifieur interne : 000047 ( Main/Exploration ); précédent : 000046; suivant : 000048Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)
Auteurs : RBID : ISTEX:706_1996_Article_BF00807577.pdfEnglish descriptors
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Abstract
A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol,8) has been developed. In the key step of the reaction sequence, the indium mediated allylation ofD-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.
DOI: 10.1007/BF00807577
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Schmid</name><affiliation wicri:level="1"><mods:affiliation>Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria</mods:affiliation><country xml:lang="fr">Autriche</country><wicri:regionArea>Institut für Organische Chemie, Universität Wien, A-1090, Wien</wicri:regionArea><wicri:noRegion>Wien</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="RBID">ISTEX:706_1996_Article_BF00807577.pdf</idno><date when="1996">1996</date><idno type="doi">10.1007/BF00807577</idno><idno type="wicri:Area/Main/Corpus">000443</idno><idno type="wicri:Area/Main/Curation">000443</idno><idno type="wicri:Area/Main/Exploration">000047</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>3-Deoxy-D-arabino-2-heptulose (Kamusol)</term><term>3-Deoxy-D-arabino-2-heptulosonic acid</term><term>Indium mediated allylation</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="eng">A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol,8) has been developed. In the key step of the reaction sequence, the indium mediated allylation ofD-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.</div></front></TEI><mods xsi:schemaLocation="http://www.loc.gov/mods/v3 file:///applis/istex/home/loadistex/home/etc/xsd/mods.xsd" version="3.4" istexId="4cead96e9e8d27a72241a598ccdddb4ba1846ed6"><titleInfo lang="eng"><title>Indium mediated allylation in carbohydrate chemistry: A convenient synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-arabino-2-heptulose (kamusol)</title></titleInfo><titleInfo lang="ger"><title>Indiumunterstützte Allylierung in der Kohlenhydratchemie: Eine einfache Synthese von 3-Desoxy-D-arabino-2-heptulosonsäure (DAH) und 3-Desoxy-D-arabino-2-heptulose (Kamusol)</title></titleInfo><name type="personal"><namePart type="given">R. H.</namePart><namePart type="family">Prenner</namePart><role><roleTerm type="text">author</roleTerm></role><affiliation>Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria</affiliation></name><name type="personal"><namePart type="given">W.</namePart><namePart type="family">Schmid</namePart><role><roleTerm type="text">author</roleTerm></role><affiliation>Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria</affiliation></name><typeOfResource>text</typeOfResource><genre>Organische Chemie Und Biochemie</genre><genre>Original Paper</genre><originInfo><publisher>Springer-Verlag, Vienna</publisher><dateCreated encoding="w3cdtf">1996-03-03</dateCreated><dateCaptured encoding="w3cdtf">1996-03-13</dateCaptured><dateValid encoding="w3cdtf">2004-11-28</dateValid><copyrightDate encoding="w3cdtf">1996</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="eng">A short and economical synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (4) and 3-deoxy-D-arabino-2-heptulose (kamusol,8) has been developed. In the key step of the reaction sequence, the indium mediated allylation ofD-erythrose in an aqueous solvent system was utilized generating a seven carbon backbone which was further transformed into the title compounds.</abstract><abstract lang="ger">Eine kurzer und ökonomischer Syntheseweg für 3-Desoxy-D-arabino-2-heptulosonsäure (4) und 3-Desoxy-D-arabino-2-heptulose (Kamusol,8) wurde entwickelt. Im Schlüsselschritt der Synthesesequenz wurde die indiumunterstützte Allylierung vonD-Erythrose in wäßrigen Reaktionsmedien angewendet. Das mittels dieser Methode auf sieben Kohlenstoffatome verlängerte Kohlenhydrat-Grundgerüst konnte einfach in die Titelverbindungen übergeführt werden.</abstract><subject lang="eng"><genre>Keywords</genre><topic>3-Deoxy-D-arabino-2-heptulosonic acid</topic><topic>3-Deoxy-D-arabino-2-heptulose (Kamusol)</topic><topic>Indium mediated allylation</topic></subject><relatedItem type="series"><titleInfo type="abbreviated"><title>Monatsh Chem</title></titleInfo><titleInfo><title>Monatshefte für Chemie / Chemical Monthly</title><partNumber>Year: 1996</partNumber><partNumber>Volume: 127</partNumber><partNumber>Number: 10</partNumber></titleInfo><genre>Archive Journal</genre><originInfo><dateIssued encoding="w3cdtf">1996-10-01</dateIssued><copyrightDate encoding="w3cdtf">1996</copyrightDate></originInfo><subject usage="primary"><topic>Chemistry</topic><topic>Chemistry/Food Science, general</topic><topic>Analytical Chemistry</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Physical Chemistry</topic><topic>Theoretical and Computational Chemistry</topic></subject><identifier type="issn">0026-9247</identifier><identifier type="issn">Electronic: 1434-4475</identifier><identifier type="matrixNumber">706</identifier><identifier type="local">IssueArticleCount: 13</identifier><recordInfo><recordOrigin>Springer-Verlag, 1996</recordOrigin></recordInfo></relatedItem><identifier type="doi">10.1007/BF00807577</identifier><identifier type="matrixNumber">Art9</identifier><identifier type="local">BF00807577</identifier><accessCondition type="use and reproduction">MetadataGrant: OpenAccess</accessCondition><accessCondition type="use and reproduction">AbstractGrant: OpenAccess</accessCondition><accessCondition type="restriction on access">BodyPDFGrant: Restricted</accessCondition><accessCondition type="restriction on access">BodyHTMLGrant: Restricted</accessCondition><accessCondition type="restriction on access">BibliographyGrant: Restricted</accessCondition><accessCondition type="restriction on access">ESMGrant: Restricted</accessCondition><part><extent unit="pages"><start>1045</start><end>1050</end></extent></part><recordInfo><recordOrigin>Springer-Verlag, 1996</recordOrigin><recordIdentifier>706_1996_Article_BF00807577.pdf</recordIdentifier></recordInfo></mods></record>Pour manipuler ce document sous Unix (Dilib)
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