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)-ß-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.
Subject(s)
Chemistry Techniques, Synthetic/methods , Methylglucosides/chemical synthesis , Organometallic Compounds/chemistry , Crystallography, X-Ray , Ferrous Compounds/chemistry , Iodine/chemistry , Ligands , Macromolecular Substances/chemistry , Magnetic Resonance Spectroscopy , Metallocenes , Methylglucosides/chemistry , Molecular Structure , X-Ray Diffraction/methodsABSTRACT
Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH(2), OH and Cl in the 2,4-triazine positions.
