Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf

Figure optionsDownload as PowerPoint slideN-(p-Methylphenylthio)-ε-caprolactam (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides an efficient thiophilic promoter system, capable of activating different thioglycosides. Both ‘armed’ and ‘disarmed’ thioglycosyl donors were activated for glycosidic bond formation. Notably, this reagent combination works well in reactivity-based one-pot oligosaccharide assembly strategy.

Figure optionsDownload as PowerPoint slideHighlights
► N-(p-Methylphenylthio)-ε-caprolactam-TMSOTf acts as efficient activator for glycosylation reaction based on thioglycosides.
► Both armed and disarmed thioglycosyl donors are activated.
► The reagent system works well in reactivity based one-pot oligosaccharide assembly.