Russ, Carolin and Ilgen, Florian and Reil, Christian and Luff, Claudia and Begli, Alireza Haji and Koenig, Burkhard (2011) Efficient preparation of beta-D-glucosyl and beta-D-mannosyl ureas and other N-glucosides in carbohydrate melts. GREEN CHEMISTRY, 13 (1). pp. 156-161. ISSN 1463-9262,
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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, beta-D-glucosyl- and beta-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 beta-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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SALT MIXTURES; SUGAR; SOLVENTS; GLYCOSYLUREAS; SURFACTANTS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 29 Jun 2020 06:23 |
| Last Modified: | 29 Jun 2020 06:23 |
| URI: | https://pred.uni-regensburg.de/id/eprint/21452 |
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