Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions
Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions
No Thumbnail Available
Files
There are no files associated with this item.
Date
2019
Authors
Liu, Hui
Hansen, Thomas
Zhou, Si-Yu
Wen, Guo-En
Liu, Xu-Xue
Zhang, Qing-Ju
Codée, Jeroen D. C.
Sun, Jian-Song
Editors
Journal ISSN
Electronic ISSN
ISBN
Bibliographical data
Publisher
Series
DOI (citable link)
International patent number
Link to the license
oops
EU project number
Project
Open Access publication
Collections
Title in another language
Publication type
Journal article
Publication status
Published
Published in
Organic Letters ; 21 (2019), 21. - pp. 8713-8717. - ISSN 1523-7060. - eISSN 1523-7052
Abstract
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.
Summary in another language
Subject (DDC)
540 Chemistry
Keywords
Conference
Review
undefined / . - undefined, undefined. - (undefined; undefined)
Cite This
ISO 690
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.9b03321BibTex
@article{Liu2019-11-01DualP-47666, year={2019}, doi={10.1021/acs.orglett.9b03321}, title={Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions}, 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: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/server/rdf/resource/123456789/47666"> <dc:contributor>Zhou, Si-Yu</dc:contributor> <dc:contributor>Hansen, Thomas</dc:contributor> <dcterms:issued>2019-11-01</dcterms:issued> <foaf:homepage rdf:resource="http://localhost:8080/"/> <dc:creator>Schmidt, Richard R.</dc:creator> <dc:contributor>Schmidt, Richard R.</dc:contributor> <dc:language>eng</dc:language> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-11-27T14:04:23Z</dc:date> <dc:contributor>Codée, Jeroen D. C.</dc:contributor> <dc:contributor>Zhang, Qing-Ju</dc:contributor> <dc:contributor>Liu, Xu-Xue</dc:contributor> <dc:creator>Zhang, Qing-Ju</dc:creator> <dc:creator>Liu, Hui</dc:creator> <dc:contributor>Sun, Jian-Song</dc:contributor> <dc:creator>Sun, Jian-Song</dc:creator> <dc:creator>Zhou, Si-Yu</dc:creator> <dcterms:title>Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions</dcterms:title> <dc:creator>Codée, Jeroen D. C.</dc:creator> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-11-27T14:04:23Z</dcterms:available> <dc:contributor>Wen, Guo-En</dc:contributor> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/47666"/> <dc:creator>Liu, Xu-Xue</dc:creator> <dc:creator>Hansen, Thomas</dc:creator> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <dc:creator>Wen, Guo-En</dc:creator> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <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> <dc:contributor>Liu, Hui</dc:contributor> </rdf:Description> </rdf:RDF>
Internal note
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Examination date of dissertation
Method of financing
Comment on publication
Alliance license
Corresponding Authors der Uni Konstanz vorhanden
International Co-Authors
Bibliography of Konstanz
Yes
Refereed
Yes