title: 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.
authors.affiliation: University of Hamburg, Institute for Inorganic and Applied Chemistry, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
authors.forename: Dirk
authors.initials: D
authors.lastname: Schwidom
authors.forename: Mirjam
authors.initials: M
authors.lastname: Volkmann
authors.forename: Anne
authors.initials: A
authors.lastname: Wolter
authors.forename: Jürgen
authors.initials: J
authors.lastname: Heck
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008024:Ligands; D046911:Macromolecular Substances / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D000075163:Metallocenes; D008757:Methylglucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction / Q000379:methods
chemical_list: D005296:Ferrous Compounds; D008024:Ligands; D046911:Macromolecular Substances; D000075163:Metallocenes; D008757:Methylglucosides; D009942:Organometallic Compounds; C013108:metallocene; C016721:ruthenocene; C027020:methylglucoside; D007455:Iodine; C004998:ferrocene