title: Beta-anomeric selectivity in the glycosidation of D-mannofuranurono-6,3-lactone catalyzed by boron trifluoride diethyl etherate.
abstract: The BF3-promoted glycosylation of D-mannofuranurono-6,3-lactone with dodecanol or methanol afforded n-alkyl beta-D-mannofuranosidurono-6,3-lactone. Reduction of n-dodecyl beta-D-mannofuranosidurono-6,3-lactone with sodium borohydride yielded the corresponding alkyl beta-D-mannofuranoside.
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, UMR CNRS 6052, Synthèses et Activations de Biomolécules, Institut de Chimie de Rennes, Avenue du Général Leclerc, F-35700, Rennes, France.
authors.forename: Myriam
authors.initials: M
authors.lastname: Roussel
authors.forename: Stéphane
authors.initials: S
authors.lastname: Moutard
authors.forename: Bruno
authors.initials: B
authors.lastname: Perly
authors.forename: Martine
authors.initials: M
authors.lastname: Lefeuvre
authors.forename: Thierry
authors.initials: T
authors.lastname: Benvegnu
authors.forename: Daniel
authors.initials: D
authors.lastname: Plusquellec
mesh_terms: D001880:Boranes; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001880:Boranes; C478187:D-mannofuranurono-6,3-lactone; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides; C101707:boron trifluoride etherate