THE ASYMMETRIC DIHYDROXYLATION OF SOME ALKENYL 2-ACETYLAMINO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES - THE PREPARATION OF OPTICALLY PURE EPOXIDES AS PUTATIVE INHIBITORS OF CHITINASES

Various alkenyl 2-acetylamino-2-deoxy-beta-D-glucopyranosid have been subjected to the Sharpless asymmetric dihydroxylation protocol to yiel d the corresponding diols, albeit with somewhat disappointing stereose lectivity. An alternative, more traditional approach has yielded the o ptically pure epoxyalkyl 2-acetylamino-2-deoxy-beta-D-glucopyranosid a s putative inhibitors of chitinases. As well, an epoxypropyl chito-bio side and -trioside have been prepared, each as mixtures of two diaster eoisomers.