New method demonstrates high β-selectivity for O-glycosylation of glycals, implicating efficient synthesis of d-glucal derivatives.
The highly stereoselective sulfenylative O-glycosylation of glycals, enabled by hexafluoroisopropyl alcohol (HFIP), has been successfully developed for the first time. This methodology is compatible with three types of oxygen nucleophiles, including alkyl alcohols, phenols, and water. Glycal derivatives such as D-galactal, D-arabinal, L-fucal, and d-glucal are suitable substrates for this reaction system. A range of 2-phenylthio-O-glycosides were obtained in moderate to excellent yields with excellent β-selectivity (β:α > 20:1), including those bearing disaccharide structures. The thioether group at the C-2 position of the glycosides can be readily removed to afford the corresponding 2-deoxy-β-glycosides, which were efficiently synthesized in good yields.
No takes yet. Share an insight, caveat, or question.
Huang et al. (2025) studied this question.
Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context: