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Ruß, C. ; Ilgen, Florian ; Reil, Christian ; Luff, C. ; Haji Begli, A. ; König, Burkhard

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.



Beteiligte Einrichtungen


Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftGreen Chemistry
Verlag:Royal Society of Chemistry
Band:13
Nummer des Zeitschriftenheftes oder des Kapitels:1
Seitenbereich:S. 156-161
Datum2011
InstitutionenChemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identifikationsnummer
WertTyp
10.1039/C0GC00468EDOI
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-190576
Dokumenten-ID19057

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