Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation.

ABSTRACT: C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of β-linked C-glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C-glycoside analogues of β-glycoconjugates, including C-disaccharide mimetics.

SUBMITTER: Ling J 

PROVIDER: S-EPMC7054165 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature