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Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine

Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine

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WITTMANN, Valentin, Dirk LENNARTZ, 2002. Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine. In: European Journal of Organic Chemistry(8), pp. 1363-1367. ISSN 0075-4617. eISSN 0365-5490

@article{Wittmann2002Coppe-9896, title={Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine}, year={2002}, number={8}, issn={0075-4617}, journal={European Journal of Organic Chemistry}, pages={1363--1367}, author={Wittmann, Valentin and Lennartz, Dirk} }

<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/123456789/9896"> <dcterms:rights rdf:resource="https://creativecommons.org/licenses/by-nc-nd/2.0/legalcode"/> <dcterms:issued>2002</dcterms:issued> <dcterms:abstract xml:lang="eng">2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acetamido- 2-deoxy-β-D-glucopyranosides in 36-92% yield. The reaction conditions are milder than those previously described for oxazoline activation employing p-toluenesulfonic acid or ferric chloride. Treatment of the oxazoline with trimethylsilyl azide (22) and CuCl2 leads to 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (23) in 69% yield.</dcterms:abstract> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:09Z</dcterms:available> <dc:rights>deposit-license</dc:rights> <dc:contributor>Wittmann, Valentin</dc:contributor> <dcterms:title>Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine</dcterms:title> <dc:creator>Wittmann, Valentin</dc:creator> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:09Z</dc:date> <dc:creator>Lennartz, Dirk</dc:creator> <dcterms:bibliographicCitation>First publ. in: European Journal of Organic Chemistry 2002, pp. 1363-1367</dcterms:bibliographicCitation> <dc:contributor>Lennartz, Dirk</dc:contributor> <dc:language>eng</dc:language> <dc:format>application/pdf</dc:format> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9896"/> </rdf:Description> </rdf:RDF>

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