Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates


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GENG, Yiqun, Amit KUMAR, Hassan M. FAIDALLAH, Hassan A. ALBAR, Ibrahim A. MHKALID, Richard SCHMIDT, 2013. Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates. In: European Journal of Organic Chemistry. 2013(31), pp. 7035-7040. ISSN 1434-193X. eISSN 0365-5490. Available under: doi: 10.1002/ejoc.201301116

@article{Geng2013Organ-26064, title={Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates}, year={2013}, doi={10.1002/ejoc.201301116}, number={31}, volume={2013}, issn={1434-193X}, journal={European Journal of Organic Chemistry}, pages={7035--7040}, author={Geng, Yiqun and Kumar, Amit and Faidallah, Hassan M. and Albar, Hassan A. and Mhkalid, Ibrahim A. and Schmidt, Richard} }

<rdf:RDF xmlns:dcterms="" xmlns:dc="" xmlns:rdf="" xmlns:bibo="" xmlns:dspace="" xmlns:foaf="" xmlns:void="" xmlns:xsd="" > <rdf:Description rdf:about=""> <dc:creator>Albar, Hassan A.</dc:creator> <dcterms:isPartOf rdf:resource=""/> <dc:creator>Geng, Yiqun</dc:creator> <dc:contributor>Geng, Yiqun</dc:contributor> <dcterms:title>Organocatalysis for the Acid-Free O-Arylidenation of Carbohydrates</dcterms:title> <dc:language>eng</dc:language> <dc:creator>Mhkalid, Ibrahim A.</dc:creator> <dc:rights>terms-of-use</dc:rights> <dc:creator>Faidallah, Hassan M.</dc:creator> <dc:contributor>Albar, Hassan A.</dc:contributor> <dc:date rdf:datatype="">2014-01-31T10:57:05Z</dc:date> <dc:creator>Kumar, Amit</dc:creator> <dcterms:available rdf:datatype="">2014-01-31T10:57:05Z</dcterms:available> <dc:contributor>Faidallah, Hassan M.</dc:contributor> <dc:contributor>Schmidt, Richard</dc:contributor> <dcterms:abstract xml:lang="eng">Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed.</dcterms:abstract> <dc:creator>Schmidt, Richard</dc:creator> <dspace:isPartOfCollection rdf:resource=""/> <dcterms:issued>2013</dcterms:issued> <dcterms:rights rdf:resource=""/> <dcterms:bibliographicCitation>European Journal of Organic Chemistry ; (2013), 31. - S. 7035-7040</dcterms:bibliographicCitation> <dc:contributor>Mhkalid, Ibrahim A.</dc:contributor> <bibo:uri rdf:resource=""/> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:contributor>Kumar, Amit</dc:contributor> </rdf:Description> </rdf:RDF>

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