The synthesis of polymerizable vinyl sugars

In this feature article we review the synthesis of polymerizable vinyl sugars. Many such syntheses start from isopropylidene-protected sugars, which still have a free OH-group. These compounds are then converted to polymerizable monomers by esterification or etherification. Selective reactions at non-protected sugars, introducing polymerizable groups, can be achieved by enzymatic catalysis. Alternatively, such selective transformations may be accomplished by chemical reaction at the reducing group of the sugar either directly or after transforming the half-acetal to a more reactive intermediate. Furthermore, results are described on the synthesis of vinyl sugars whose vinyl group is connected with the monosaccharide by a C-C bond. Such monomers can be polymerized by radical as well as by anionic initiation. In this case a chemically very stable connection is obtained in the resulting polymers between the sugar moiety and the polymer backbone.