Combined catalytic conversion involving an enzyme, a homogeneous and a heterogeneous catalyst: one-pot preparation of 4-deoxy-D-glucose derivatives from D-galactose

Consecutive catalytic oxidation (oxygen, D-galactose oxidase), dehydration (L-proline) and reduction (hydrogen, palladium) of methyl beta-D-galactoside in water at neutral pH yielded methyl 4-deoxy-6-aldehydo-beta-D-glucoside without intermediate recovery steps demonstrating the potential power of a multi-catalytic approach, using both bio- and chemo-catalysts, for carbohydrate conversions without the use of protective groups or stoichiometric amounts of reagents. (C) 2002 Elsevier Science Ltd. All rights reserved.