The major challenge in carbohydrate synthesis is stereochemical control of glycosidic bond formation. Different glycosylation methods have been developed that are based on the modulation effect of external nucleophiles. This review highlights the development, synthetic application, challenges and outlook of the modulated glycosylation methods.
The chemical properties of nucleophile additives were investigated in a modulated glycosylation context. N-Formylmorpholine (NFM) was found to be an effective modulator for glycosylation with less reactive 2-azido-2-deoxythioglucosyl and thiogalactosyl donors.
We reported a remote control glycosylation method using the picoloyl protecting group for 2-deoxy-β-glycosidic bond formation. The method is applicable to various 2-deoxythioglycosyl donors and the utility is illustrated by the synthesis of a deoxytrisaccharide component of landomycins.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.