Nitrosation of sugar oximes : preparation of 2-glycosyl-1-hydroxydiazene-2-oxides

Brand, Jörg; Huhn, Thomas; Groth, Ulrich; Jochims, Johannes

Nitrosation of sugar oximes : preparation of 2-glycosyl-1-hydroxydiazene-2-oxides

Dateien

Nitrosation_of_sugar_oximes.pdfGröße: 230.63 KBDownloads: 380

Datum

2005

Autor:innen

Brand, Jörg

Huhn, Thomas

Groth, Ulrich

Jochims, Johannes

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Chemistry - A European Journal. 2005, 12(2), pp. 499-509. ISSN 0947-6539. Available under: doi: 10.1002/chem.200500325

Zusammenfassung

Oximes of glucose, xylose, lactose, fructose, and mannose have been prepared. Nitrosation of the oximes of glucose, xylose, and lactose with NaNO2/HCl afforded 2-(-glycopyranosyl)-1-hydroxydiazene-2-oxides, which were isolated as salts 13, 22, and 28. Nitrosation of fructose oxime 29 furnished fructose, whereas nitrosation of mannose oxime 30 with NaNO2/HCl afforded the 1-hydroxy-2-(-d-mannopyranosyl)diazene-2-oxide 32, from which the p-anisidinium salt 31 and the sodium salt 33 were prepared. However, nitrosation of 30 with isopentyl nitrite in aqueous solutions of CsOH or KOH resulted in the formation of the 2-(-D-mannofuranosyl)-1-hydroxydiazene-2-oxide salts 34 and 35, respectively. Methylation of the ammonium 2-(-D-glucopyranosyl)-1-hydroxydiazene-2-oxide 13 yielded the 1-methoxy compound, which was benzoylated to afford the tetra-O-benzoate 14 a, the structure of which was confirmed by X-ray diffraction analysis. From the glucose O-methyloximes 15 and 16 the N-methoxy-N-nitroso-2,3,4,6-tetra-O-acetyl--D-glucopyranosylamine 18 was prepared. The structure of this compound was confirmed by X-ray diffraction analysis. Treatment of acetobromoglucose with cupferron furnished the 1-(2,3,4,6-tetra-O-acetyl--D-glucopyranosyloxy)-2-phenyldiazene-2-oxide 20.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

carbohydrates, glycosyl oximes, nitrosation, NO donors, X-ray diffraction

Zitieren

ISO 690

BRAND, Jörg, Thomas HUHN, Ulrich GROTH, Johannes JOCHIMS, 2005. Nitrosation of sugar oximes : preparation of 2-glycosyl-1-hydroxydiazene-2-oxides. In: Chemistry - A European Journal. 2005, 12(2), pp. 499-509. ISSN 0947-6539. Available under: doi: 10.1002/chem.200500325

BibTex

@article{Brand2005-12-23Nitro-9984,
  year={2005},
  doi={10.1002/chem.200500325},
  title={Nitrosation of sugar oximes : preparation of 2-glycosyl-1-hydroxydiazene-2-oxides},
  number={2},
  volume={12},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={499--509},
  author={Brand, Jörg and Huhn, Thomas and Groth, Ulrich and Jochims, Johannes}
}

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/123456789/9984">
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:45Z</dcterms:available>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9984/1/Nitrosation_of_sugar_oximes.pdf"/>
    <dcterms:abstract xml:lang="eng">Oximes of glucose, xylose, lactose, fructose, and mannose have been prepared. Nitrosation of the oximes of glucose, xylose, and lactose with NaNO2/HCl afforded 2-(-glycopyranosyl)-1-hydroxydiazene-2-oxides, which were isolated as salts 13, 22, and 28. Nitrosation of fructose oxime 29 furnished fructose, whereas nitrosation of mannose oxime 30 with NaNO2/HCl afforded the 1-hydroxy-2-(-d-mannopyranosyl)diazene-2-oxide 32, from which the p-anisidinium salt 31 and the sodium salt 33 were prepared. However, nitrosation of 30 with isopentyl nitrite in aqueous solutions of CsOH or KOH resulted in the formation of the 2-(-D-mannofuranosyl)-1-hydroxydiazene-2-oxide salts 34 and 35, respectively. Methylation of the ammonium 2-(-D-glucopyranosyl)-1-hydroxydiazene-2-oxide 13 yielded the 1-methoxy compound, which was benzoylated to afford the tetra-O-benzoate 14 a, the structure of which was confirmed by X-ray diffraction analysis. From the glucose O-methyloximes 15 and 16 the N-methoxy-N-nitroso-2,3,4,6-tetra-O-acetyl--D-glucopyranosylamine 18 was prepared. The structure of this compound was confirmed by X-ray diffraction analysis. Treatment of acetobromoglucose with cupferron furnished the 1-(2,3,4,6-tetra-O-acetyl--D-glucopyranosyloxy)-2-phenyldiazene-2-oxide 20.</dcterms:abstract>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/>
    <dcterms:title>Nitrosation of sugar oximes : preparation of 2-glycosyl-1-hydroxydiazene-2-oxides</dcterms:title>
    <dc:format>application/pdf</dc:format>
    <dc:contributor>Jochims, Johannes</dc:contributor>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:45Z</dc:date>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights>
    <dc:creator>Huhn, Thomas</dc:creator>
    <dc:creator>Brand, Jörg</dc:creator>
    <dc:contributor>Brand, Jörg</dc:contributor>
    <dc:creator>Jochims, Johannes</dc:creator>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9984/1/Nitrosation_of_sugar_oximes.pdf"/>
    <dc:language>eng</dc:language>
    <dc:contributor>Groth, Ulrich</dc:contributor>
    <dc:contributor>Huhn, Thomas</dc:contributor>
    <dcterms:bibliographicCitation>First publ. in: Chemistry : a European journal ; 12 (2006), 2. - S. 499-509</dcterms:bibliographicCitation>
    <dc:creator>Groth, Ulrich</dc:creator>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9984"/>
    <dcterms:issued>2005-12-23</dcterms:issued>
  </rdf:Description>
</rdf:RDF>

Universitätsbibliographie

Ja