Group 8 metallocenes as bulky functional groups in glucopyranosides

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 1H and 13C NMR spectroscopy, by crystal structure determination as well as elemental analysis.

Figure optionsDownload as PowerPoint slide