Beta-anomeric selectivity in the glycosidation of D-mannofuranurono-6,3-lactone catalyzed by boron trifluoride diethyl etherate.
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.
Roussel
Myriam
M
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.
Moutard
Stéphane
S
Perly
Bruno
B
Lefeuvre
Martine
M
Benvegnu
Thierry
T
Plusquellec
Daniel
D
D001880:Boranes; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007783:Lactones / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism
D001880:Boranes; C478187:D-mannofuranurono-6,3-lactone; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides; C101707:boron trifluoride etherate