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 sugar s, which still have a free OH-group. These compounds are then converte d to polymerizable monomers by esterification or etherification. Selec tive reactions at non-protected sugars, introducing polymerizable grou ps, can be achieved by enzymatic catalysis. Alternatively, such select ive transformations may be accomplished by chemical reaction at the re ducing group of the sugar either directly or after transforming the ha lf-acetal to a more reactive intermediate. Furthermore, results are de scribed on the synthesis of vinyl sugars whose vinyl group is connecte d with the monosaccharide by a C-C bond. Such monomers can be polymeri zed by radical as well as by anionic initiation. In this case a chemic ally very stable connection is obtained in the resulting polymers betw een the sugar moiety and the polymer backbone.