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In our recently developed interrupted Pummerer reaction mediated (IPRm) glycosylation with S-2-[(propan-2-yl)sulfinyl] benzyl (SPSB) glycosides as glycosyl donors, the anomeric leaving groups were ...

Attachment of various 3-aminodeoxy sugars to natural products or drugs is a prominent method for new drug development. However, access to structurally diversified 3-aminodeoxy sugars and glycosylation with aglycons are challenging. We synthesized a variety of unnatural 3-aminodeoxy sugars via diversified functionalization of a common glycal intermediate bearing a cyclic sulfamidate ketimine moiety. Based on these results, the α-selective glycosylation reactions of these 3-aminodeoxy sugars and the structural modification of diosgenin were further investigated.

A diversified synthesis of 3-aminosugar analogues of digitoxin and digoxin with potent anticancer activities was explored. The synthesis was based on a highly efficient gold-catalyzed glycosylation reaction with alkynylbenzoate 3-aminoglycosides as glycosyl donors. According to this strategy, a small library containing digitoxin and digoxin analogues with various 3-aminosugar scaffolds was successfully constructed.