Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine

Wittmann, Valentin; Lennartz, Dirk

Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine

Dateien

CopperII_mediated_activation_of_sugar_oxazolines.pdfGröße: 246.45 KBDownloads: 306

Datum

2002

Autor:innen

Wittmann, Valentin

Lennartz, Dirk

URI (zitierfähiger Link)

http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-43761

Link zur Lizenz

Attribution-NonCommercial-NoDerivs 2.0 Generic

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

European Journal of Organic Chemistry. 2002(8), pp. 1363-1367. ISSN 0075-4617. eISSN 0365-5490

Zusammenfassung

2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acetamido- 2-deoxy-β-D-glucopyranosides in 36-92% yield. The reaction conditions are milder than those previously described for oxazoline activation employing p-toluenesulfonic acid or ferric chloride. Treatment of the oxazoline with trimethylsilyl azide (22) and CuCl2 leads to 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (23) in 69% yield.

Fachgebiet (DDC)

540 Chemie

Schlagwörter

Carbohydrates, Glycosylation, Copper, Oxazulines, Amino sugars

Zitieren

ISO 690

WITTMANN, Valentin, Dirk LENNARTZ, 2002. Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine. In: European Journal of Organic Chemistry. 2002(8), pp. 1363-1367. ISSN 0075-4617. eISSN 0365-5490

BibTex

@article{Wittmann2002Coppe-9896,
  year={2002},
  title={Copper(II)-mediated activation of sugar oxazolines : mild and efficient synthesis of beta-glycosides of N-Acetylglucosamine},
  number={8},
  issn={0075-4617},
  journal={European Journal of Organic Chemistry},
  pages={1363--1367},
  author={Wittmann, Valentin and Lennartz, Dirk}
}

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Universitätsbibliographie

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