Beta-anomeric selectivity in the glycosidation of D-mannofuranurono-6,3-lactone catalyzed by boron trifluoride diethyl etherate.

Carbohydr Res

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.

Published: February 2003

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.

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http://dx.doi.org/10.1016/s0008-6215(02)00439-1DOI Listing

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