Acyl Glycosides through Stereospecific Glycosyl Cross-Coupling: Rapid Access to C(sp³)-Linked Glycomimetics.

ABSTRACT: Replacement of a glycosidic bond with hydrolytically stable C-C surrogates is an efficient strategy to access glycomimetics with improved physicochemical and pharmacological properties. We describe here a stereoretentive cross-coupling reaction of glycosyl stannanes with C(sp²)- and C(sp³)-thio(seleno)esters suitable for the preparation C-acyl glycosides as synthetic building blocks to obtain C(sp³)-linked and fluorinated glycomimetics. First, we identified a set of standardized conditions employing a Pd(0) precatalyst, CuCl additive, and phosphite ligand that provided access to C-acyl glycosides without deterioration of anomeric integrity and decarbonylation of the acyl donors (>40 examples). Second, we demonstrated that C(sp³)-gly

SUBMITTER: Zhu F 

PROVIDER: S-EPMC6311691 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature