The focus of this research is the development of efficient methods for the preparation of functionalized thio- and phosphoglycosides and to use these glycosides for diastereoselective synthesis of oligosaccharides. The focus of the educational plan involves the development of programs, laboratories and group activities that foster learning as an active rather than passive activity. Collaborative learning will be stressed. With this CAREER award, the Synthetic Organic Program is supporting the research and educational plan of Dr. Kang Zhao of the Department of Chemistry at New York University. Professor Zhao will focus his research efforts on the development of an automated protocol that allows the coupling of a variety of reactivity- modulated glycosyl donors with acceptors on solid supports. The focus of Professor Zhao's educational plan involves the development of programs laboratories and group activities that foster learning as an active rather than passive activity. Collaborative learning will be stressed.