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Efficient preparation of β-D-glucosyl and β-D-mannosyl ureas and other N-glucosides in carbohydrate melts
Ruß, C., Ilgen, Florian, Reil, Christian, Luff, C., Haji Begli, A. und König, Burkhard (2011) Efficient preparation of β-D-glucosyl and β-D-mannosyl ureas and other N-glucosides in carbohydrate melts. Green Chemistry 13 (1), S. 156-161.Veröffentlichungsdatum dieses Volltextes: 14 Jan 2011 09:59
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.19057
Zusammenfassung
Sugar melts or solvent-free systems have been used to react simple unprotected hexoses at the C-1 atom with urea and urea derivatives to sugar-ureides by acid catalysis and with short reaction times. In one step, β-D-glucosyl- and β-D-mannosyl urea 2a/b were obtained in high yields. D-Galactose 6, N-acetyl-D-glucosamine 7, L-rhamnose 8 and 2-deoxy-D-glucose 9 were converted likewise to glycosyl ...
Sugar melts or solvent-free systems have been used to react simple unprotected hexoses at the C-1 atom with urea and urea derivatives to sugar-ureides by acid catalysis and with short reaction times. In one step, β-D-glucosyl- and β-D-mannosyl urea 2a/b were obtained in high yields. D-Galactose 6, N-acetyl-D-glucosamine 7, L-rhamnose 8 and 2-deoxy-D-glucose 9 were converted likewise to glycosyl ureas. Additionally, urea-related nucleophiles were investigated as melt components. N,N′-Ethylene urea 15, N,N′-allylurea 16 and ethyl carbamate 18 were β-selectively converted with D-glucose in good yield, giving the corresponding N-glycosides. Under these conditions, however, the condensation product with N-octylurea 17 was not accessible.
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| Dokumentenart | Artikel | ||||
| Titel eines Journals oder einer Zeitschrift | Green Chemistry | ||||
| Verlag: | Royal Society of Chemistry | ||||
|---|---|---|---|---|---|
| Band: | 13 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 1 | ||||
| Seitenbereich: | S. 156-161 | ||||
| Datum | 2011 | ||||
| Institutionen | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identifikationsnummer |
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| Dewey-Dezimal-Klassifikation | 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status | Veröffentlicht | ||||
| Begutachtet | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden | Ja | ||||
| URN der UB Regensburg | urn:nbn:de:bvb:355-epub-190576 | ||||
| Dokumenten-ID | 19057 |
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