Oligosaccharide synthesis in solution and on solid support with glycosyl phosphates

The synthesis of glycosyl 1-phosphate triesters and their use in solution-phase and solid-phase oligosaccharide chemistry is reviewed. The preparation of anomeric phosphates from lactol and glycal starting materials and their application in the synthesis of nucleotide diphosphate sugars is described. Glycosyl phosphates have been employed successfully in the construction of O- and C-glycosides and give highly trans-selective coupling products even in the absence of C-2 participating groups. Solid-phase techniques utilizing glycosyl phosphate triesters have enabled the assembly of biologically important complex carbohydrates. Most recently, glycosyl phosphates have been the basis for the development of an automated oligosaccharide synthesizer.