Protecting Group Strategies in Carbohydrate Chemistry

Carbohydrates are the most densely functionalized class of biopolymers in nature. This chapter describes the differences in the reactivity of the various functional groups on a carbohydrate ring and how to exploit these in the design of effective protecting group strategies. It then describes how protecting group effects can be used to control stereoselective transformations and reactivity‐controlled one‐pot synthesis strategies. The chapter highlights applications and strategies in automated synthesis. Different strategies have been developed to automate oligosaccharide assembly based on either solution‐phase synthesis or solid‐phase techniques, and automated solid‐phase synthesizers are now commercially available. Protecting group chemistry can make or break any (oligo)saccharide synthesis effort. The impact of protecting groups on the stereochemical outcome of a glycosylation reaction is best illustrated by the anchimeric assistance that neighboring groups can provide during a glycosylation reaction.