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

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Datum

2005

Autor:innen

Brand, Jörg

Huhn, Thomas

Groth, Ulrich

Jochims, Johannes

Publikationstyp

Zeitschriftenartikel

unikn.publication.listelement.citation.prefix.version.undefined

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}
}

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    <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>
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