Design and Synthesis of Benzimidazole-Iminosugars and Their Inhibitory Activities against Glycosidases

Efficient one-pot synthesis of the unexpected fused multicyclic iminosugars by an aza-Diels–Alder mechanism

“…However, there was just one example of the use of aromatic amine to construct the tricyclic benzimidazole-fused iminosugar 4 catalyzed by Sc(OTf) 3 . 11 Inspired by this case and as a continuation of our studies on bioactive fused multicyclic iminosugars, 14 herein, we report the synthesis of a series of unexpected and directly deprotected complex iminosugars 5 by a one-pot Yb(OTf) 3 -catalyzed reaction of d -ribose tosylate and different anilines (Scheme 1). In general, directly obtaining deprotected saccharides has been difficult in multistep synthetic saccharide research because of the installation and removal of specific protective groups.…”