H. Brunner, Max Schönherr, M. Zabel
Oct 30, 2001
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Journal
Tetrahedron-asymmetry
Abstract
Abstract A new way of linking carbohydrates to phosphorus- or nitrogen-containing aldehydes via oxime ethers is described resulting in novel CN 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.