Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis

Lade...
Vorschaubild
Dateien
kumar_216329.pdf
kumar_216329.pdfGröße: 347.1 KBDownloads: 302
Datum
2012
Herausgeber:innen
Kontakt
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
ArXiv-ID
Internationale Patentnummer
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Green
Sammlungen
Core Facility der Universität Konstanz
Gesperrt bis
Titel in einer weiteren Sprache
Forschungsvorhaben
Organisationseinheiten
Zeitschriftenheft
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
European Journal of Organic Chemistry. 2012, 2012(14), pp. 2715-2719. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201200138
Zusammenfassung

Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β-selective. An SN2-type reaction course under acid/base catalysis is invoked by these and previous results.

Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
Schlagwörter
Carbohydrates, Glycosylation, Thioglycosylation, Reaction mechanisms
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690KUMAR, Amit, Richard R. SCHMIDT, 2012. Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis. In: European Journal of Organic Chemistry. 2012, 2012(14), pp. 2715-2719. ISSN 1434-193X. eISSN 1099-0690. Available under: doi: 10.1002/ejoc.201200138
BibTex
@article{Kumar2012Rever-21632,
  year={2012},
  doi={10.1002/ejoc.201200138},
  title={Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis},
  number={14},
  volume={2012},
  issn={1434-193X},
  journal={European Journal of Organic Chemistry},
  pages={2715--2719},
  author={Kumar, Amit and Schmidt, Richard R.}
}
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/123456789/21632">
    <dcterms:issued>2012</dcterms:issued>
    <dc:language>eng</dc:language>
    <dc:creator>Schmidt, Richard R.</dc:creator>
    <dc:contributor>Schmidt, Richard R.</dc:contributor>
    <dc:rights>terms-of-use</dc:rights>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-02-13T09:09:22Z</dc:date>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/21632/2/kumar_216329.pdf"/>
    <dcterms:abstract xml:lang="eng">Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reactions with phenylboron difluoride as catalyst are highly β-selective. An SN2-type reaction course under acid/base catalysis is invoked by these and previous results.</dcterms:abstract>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/21632/2/kumar_216329.pdf"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:contributor>Kumar, Amit</dc:contributor>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Kumar, Amit</dc:creator>
    <dcterms:bibliographicCitation>European Journal of Organic Chemistry ; (2012), 14. - S. 2715-2719</dcterms:bibliographicCitation>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2013-08-14T22:25:05Z</dcterms:available>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/21632"/>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dcterms:title>Reversal of Anomeric Selectivity with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Thiols as Acceptors Under Acid/Base Catalysis</dcterms:title>
  </rdf:Description>
</rdf:RDF>
Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Kontakt
URL der Originalveröffentl.
Prüfdatum der URL
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Begutachtet
Diese Publikation teilen