ABSTRACT

This chapter addresses the chemical synthesis of C-disaccharides and non C-disaccharidic compounds, since these compounds may also possess biological activity making synthetic efforts toward these compounds worthwhile. A C-disaccharide is characterized by having a carbon atom linker instead of the normal oxygen atom. Strictly speaking, the product is not a C-disaccharide since two carbon atoms are linking the sugars together. Hydrolysis of the isopropylidene groups allows a 5- or 6-exo closure of the appropriate hydroxyl onto the nitro olefin to give the C-disaccharides. Vogel and Bimwala have also assembled C-disaccharides by intramolecular radical addition. Y. Kishi has been very active in the area of both C-glycoside synthesis and C-disaccharide synthesis. His C-disaccharide program has been concerned not only with the assembly of C-disaccharides, but also with the study of their conformation in solution11 and their comparision to the solution conformation of O-disaccharides.