This proposal brings together two PI's and their laboratories with distinct but overlapping expertise in the glycochemistry, both from the metropolitan Detroit area, with the aim of developing new and robust technology and methodology for the synthesis of oligosaccharides and their conjugates, such as might be readily applied by non- specialists. The proposal focuses on biologically active oligosaccharides from the microbial glycome and selects particular targets based on the biological relevance and the chemical challenges they present. The proposal aims to develop new, improved, and robust general technologies and methodology for glycosylation that will make glycosylation both more efficient and less wasteful in terms of resources. According to this paradigm flow and microwave flow methods will be developed for the preparation of glycosyl donors, acceptors and promotors, and their eventual use in scalable glycosylation reactions. These technologies will be applied to existing methodologies for glycosidic bond formation and in conjunction with the novel concepts of recyclable photochromic glycosyl donors, and of glycosyl donors that are only activated on demand in the confines of a supramolecular complex combining the donor, acceptor and activator. The proposal seeks to make all building blocks, promotors and oligosaccharides on larger scales than have heretofore been possible and to make the so-formed materials available for use in the broader community, especially by non- specialist laboratories.