Late-Stage Oxime O-Glycosylation with Unprotected Glycosyl Fluorides

Herein, we report a straightforward approach to the late-stage oxime O-glycosylation, utilizing unprotected glycosyl fluoride donors under basic aqueous conditions. By employing a diverse array of commercially available aryl/alkyl oximes and modified sugar/steroid oximes, we have successfully synthesized the desired N-O-linked glycosides and oligosaccharides in satisfactory yields, while achieving specific 1,2-trans-selectivity. This approach stands out due to its broad substrate compatibility, capability for gram-scale synthesis, and potential for glyco-diversification of bioactive molecules, thus holding promise for applications in biological and pharmaceutical research.