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

Abstract

Consecutive catalytic oxidation (oxygen, d-galactose oxidase), dehydration ( l-proline) and reduction (hydrogen, palladium) of methyl β- d-galactoside in water at neutral pH yielded methyl 4-deoxy-6-aldehydo-β- 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.