Group 8 metallocenes as bulky functional groups in glucopyranosides

Abstract

The functionalization of methyl D-glucopyranosides at positions 4 and 6 with bulky moieties was carried out by using ferrocenyl and ruthenocenyl substituents. The synthesis succeeded by reaction of the methyl D-glucopyranosides with the corresponding metallocene monocarbaldehyde dimethyl acetal catalysed by iodine in acetonitrile. The resulting compounds methyl 4,6-O-(metallocenylmethylidene)-α-D-glucopyranoside (M=Fe (1) and M=Ru (3)) and methyl 4,6-O-(metallocenylmethylidene)-β-D-glucopyranoside (M=Fe (2) and M=Ru (4)) were characterized by (1)H and (13)C NMR spectroscopy, by crystal structure determination as well as elemental analysis.