405139-86-8Relevant articles and documents
Enantioselective catalysis. Part 142: Carbohydrate-derived oxime ethers from functionalised aldehydes and O-β-D-glucopyranosylhydroxylamine - New C=N ligands stable towards hydrolysis
Brunner, Henri,Schoenherr, Maximilian,Zabel, Manfred
, p. 2671 - 2675 (2001)
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-β-D-glucopyranosylhydroxylamine 2 with 2-diphenylphosphanylbenzaldehyde 3 or pyridine-2-carbaldehyde 4 afforded the oxime ethers O-(β-D-glucopyranosyl)-2-diphenylphosphanylbenzaldoxime 5 and O-(β-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-β-D-glucopyranosyl)-2- diphenylphosphanylbenzaldoxime 7 and O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)pyridine-2-carbaldoxime 8 were obtained. The molecular structure of 7 was established by X-ray diffraction studies.