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Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation

Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation

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TIWARI, Vinod K., Amit KUMAR, Richard R. SCHMIDT, 2012. Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation. In: European Journal of Organic Chemistry. 2012(15), pp. 2945-2956. ISSN 1434-193X. eISSN 1099-0690

@article{Tiwari2012Disac-21631, title={Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation}, year={2012}, doi={10.1002/ejoc.201101815}, number={15}, volume={2012}, issn={1434-193X}, journal={European Journal of Organic Chemistry}, pages={2945--2956}, author={Tiwari, Vinod K. and Kumar, Amit and Schmidt, Richard R.} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/21631"> <dcterms:title>Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation</dcterms:title> <dc:rights>deposit-license</dc:rights> <dc:contributor>Tiwari, Vinod K.</dc:contributor> <dc:creator>Tiwari, Vinod K.</dc:creator> <dc:language>eng</dc:language> <dcterms:bibliographicCitation>European Journal of Organic Chemistry ; (2012), 15. - S. 2945-2956</dcterms:bibliographicCitation> <dc:creator>Schmidt, Richard R.</dc:creator> <dc:contributor>Kumar, Amit</dc:contributor> <dcterms:issued>2012</dcterms:issued> <dc:contributor>Schmidt, Richard R.</dc:contributor> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-02-12T08:04:22Z</dc:date> <dc:creator>Kumar, Amit</dc:creator> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-08-14T22:25:05Z</dcterms:available> <dcterms:rights rdf:resource="http://nbn-resolving.org/urn:nbn:de:bsz:352-20140905103605204-4002607-1"/> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/21631"/> <dcterms:abstract xml:lang="eng">In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1- thio-D-glucopyranoside was employed as a donor, which could be readily connected by 1,3-dipolar cycloaddition (click reaction) to O-(2- or 3-azidomethylbenzyl)-protected acceptors to afford, after liberation of the accepting hydroxy groups, the desired donor–spacer–acceptor-linked intermediates. NIS/TMSOTf-promoted glycosylation furnished disaccharide-containing macrocycles. In general, very good results were obtained. The anomeric selectivity is dependent on various factors, the ring size seeming crucial.</dcterms:abstract> </rdf:Description> </rdf:RDF>

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