Thioglycosides are common building blocks used in synthesis of biomedically relevant compounds. Our group discovered an unusually reactive class of thioglycosides that we named “superarmed building blocks.” The superarming reactivity was achieved via modulating protecting groups. Despite high reactivity and potential broad application in synthesis, building blocks equipped with the superarming protecting group pattern are tedious to prepare. For example, the synthesis of superarmed thioglycosides requires six or seven synthetic steps, several chromatographic purifications of intermediates, the use of toxic reagents, and may lead to weeks of benchwork. Poor accessibility to sugar building blocks in general, hampers the development of many therapeutic agents and diagnostic platforms. Reported herein is a streamlined approach to the synthesis to super-armed building blocks equipped with thioethyl, thiophenyl, and thiotolyl anomeric leaving groups.

Dr. Demchenko was Emma's principle investigator on this project along with the graduate student Nicholas Forsythe. Dr. Demchenko was often a sounding board for ideas and helped with product identification as well as potential next steps for the project. This work could not have been done without both Dr. Demchenko and Nick's help and belief in Emma.