Programmable one-pot glycosylation

Abstract

In oligosaccharide synthesis, protecting groups, possible participating groups, promoters/catalysts, reaction conditions, and donor leaving groups and acceptors must all be carefully designed in order to generate the correct regio- and stereochemistry for the new glycosidic bond. Programmable one-pot synthesis has been developed to address the above problems. This strategy is based on the sequential use of thioglycoside building blocks to form glycosidic bonds based on the reactivity difference of the building blocks. The activation of the anomeric leaving group can be attenuated through modification of the protecting group strategy and neighboring group participation. This reactivity-based strategy has been applied to one-pot glycosylation reactions where a series of building blocks with identical leaving groups react sequentially in one vessel without laborious intermediate purification steps. It provides rapid access to oligosaccharides with a wide-range of molecular diversity. In this chapter we outline the recent development of this strategy that can be applied to synthesize a wide variety of oligosaccharides and glycoconjugates that are associated with infectious diseases or carbohydrate-based cancer antigens. © 2011 Springer-Verlag Berlin Heidelberg.