Pd-Catalyzed Stereospecific Glycosyl Cross-Coupling of Reversed Anomeric Stannanes for Modular Synthesis of Nonclassical <i>C</i>-Glycosides.

ABSTRACT: Nonclassical C-glycosides, distinguished by their unique glycosidic bond connection mode, represent a promising avenue for the development of carbohydrate-based drugs. However, the accessibility of nonclassical C-glycosides hinders broader investigations into their structural features and modes of action. Herein, we present the first example of Pd-catalyzed stereospecific glycosylation of nonclassical anomeric stannanes with aryl or vinyl halides. This method furnishes desired nonclassical aryl and vinyl C-glycosides in good to excellent yields, while allowing for exclusive control of nonclassical anomeric configuration. Of significant note is the demonstration of the generality and practicality of this nonclassical C-glycosylation approach across more than 50 e

SUBMITTER: Cheng G 

PROVIDER: S-EPMC11600346 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature