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Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions

Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions

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LIU, Hui, Thomas HANSEN, Si-Yu ZHOU, Guo-En WEN, Xu-Xue LIU, Qing-Ju ZHANG, Jeroen D. C. CODÉE, Richard R. SCHMIDT, Jian-Song SUN, 2019. Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions. In: Organic Letters. 21(21), pp. 8713-8717. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.9b03321

@article{Liu2019-11-01DualP-47666, title={Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions}, year={2019}, doi={10.1021/acs.orglett.9b03321}, number={21}, volume={21}, issn={1523-7060}, journal={Organic Letters}, pages={8713--8717}, author={Liu, Hui and Hansen, Thomas and Zhou, Si-Yu and Wen, Guo-En and Liu, Xu-Xue and Zhang, Qing-Ju and Codée, Jeroen D. C. and Schmidt, Richard R. and Sun, Jian-Song} }

<rdf:RDF xmlns:dcterms="http://purl.org/dc/terms/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#" xmlns:foaf="http://xmlns.com/foaf/0.1/" xmlns:void="http://rdfs.org/ns/void#" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/47666"> <dc:creator>Zhou, Si-Yu</dc:creator> <dc:contributor>Liu, Hui</dc:contributor> <dc:contributor>Codée, Jeroen D. C.</dc:contributor> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-11-27T14:04:23Z</dcterms:available> <dc:contributor>Sun, Jian-Song</dc:contributor> <dcterms:issued>2019-11-01</dcterms:issued> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:creator>Wen, Guo-En</dc:creator> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/47666"/> <dc:creator>Sun, Jian-Song</dc:creator> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-11-27T14:04:23Z</dc:date> <dc:creator>Codée, Jeroen D. C.</dc:creator> <dc:language>eng</dc:language> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:contributor>Schmidt, Richard R.</dc:contributor> <dc:creator>Zhang, Qing-Ju</dc:creator> <dc:creator>Hansen, Thomas</dc:creator> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:contributor>Liu, Xu-Xue</dc:contributor> <dc:contributor>Wen, Guo-En</dc:contributor> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dc:contributor>Zhou, Si-Yu</dc:contributor> <dc:creator>Liu, Xu-Xue</dc:creator> <dcterms:title>Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions</dcterms:title> <dc:creator>Schmidt, Richard R.</dc:creator> <dc:creator>Liu, Hui</dc:creator> <dc:contributor>Zhang, Qing-Ju</dc:contributor> <dc:contributor>Hansen, Thomas</dc:contributor> <dcterms:abstract xml:lang="eng">The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.</dcterms:abstract> </rdf:Description> </rdf:RDF>

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