Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis. [Display omitted] •Protecting group free activation of unprotected sugars under aqueous conditions.•Single step stereoselective synthesis of a wide variety of glycosides.•Direct formation of glycosyl oxazolines as donor substrates for enzyme catalysed reactions.•Applications to oligosaccharides isolated from natural sources.•One-pot tandem processes, such as glycosyl azide or thiol formation, and Click chemistry.