Since their isolation in the 1960s, imino sugars have attracted considerable interest from synthetic chemists, biologists, and clinical researchers. Glycomimetics in which the endocyclic oxygen of the parent glycoside is replaced by a nitrogen atom are known to be potent inhibitors of a number of enzymes of medicinal interest, such as glycosidases, glycosyltransferases, and, most recently, enzymes that act on non-sugar substrates. In the glycomimetics world, 1-deoxynojirimycin (DNJ) may be considered as the “king” of imino sugars. Indeed, since its rst synthesis, more than one thousand derivatives of DNJ have been reported in the literature, most of them being evaluated towards relevant biological targets. It is thus not surprising that the two imino sugar drugs currently on the market are based on the DNJ motif.
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Chapter 36: Large-scale synthesis of 2,3,4,6-Tetra-O-benzyl-1- By Damien Hazelard, Mathieu L. Lepage, Jérémy P. Schneider, Maëva M. Pichon, Philippe Compain, and Fabien Massicot
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