Carbohydrates are used in a number of different biological processes, which allows carbohydrate processing to be the target of therapeutic agents. Glycosidases are enzymes that catalyze the degradation of carbohydrates by hydrolyzing the glycosidic linkage. Iminosugars are homologues of carbohydrates in which the endocyclic oxygen of the sugar has been replaced by a nitrogen. Iminosugars are often useful therapeutic agents because of their ability to inhibit glycosidases. The ongoing conversion of commercially-available methyl 4,6-O-benzylidene--D-glucopyranoside into the iminosugar (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol is described.

Synthesis of a polyhydroxylated pyrrolidine from a D-glucose derivative

251st National Meeting (2016)

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