Brunner, Henri and Schoenherr, Maximilian and Zabel, Manfred (2001) Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-beta-D-glucopyranosylhydroxylamine - new C=N ligands stable towards hydrolysis. TETRAHEDRON-ASYMMETRY, 12 (19). pp. 2671-2675. ISSN 0957-4166
Full text not available from this repository. (Request a copy)Abstract
A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel C=N ligands which are stable towards hydrolysis. Reaction Of O-beta -D-glucopyranosythydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(beta -D-glucopyranosyl)pyridine-2-carbaldoxime 6. After peracetylation of the hydroxyl groups in 5 and 6, the protected sugar derivatives O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-beta -D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies. (C) 2001 Elsevier Science Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ; |
| Subjects: | 500 Science > 510 Mathematics |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Alumni or Retired Professors > Prof. Dr. Henri Brunner |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Dec 2021 14:52 |
| Last Modified: | 01 Dec 2021 14:52 |
| URI: | https://pred.uni-regensburg.de/id/eprint/41018 |
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