Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides.

摘要: The utilization of substoichiometric amounts commercially available nickel(II) triflate as an activator in the reagent-controlled glycosylation reaction for stereoselective construction biologically relevant targets containing 1,2-cis-2-amino glycosidic linkages is reported. This straightforward and accessible methodology mild, operationally simple safe through catalytic activation by readily Ni(OTf)2 comparison to systems employing our previously in-house prepared Ni(4-F-PhCN)4(OTf)2. We anticipate that bench-stable inexpensive Ni(OTf)2, coupled with little no extra laboratory training set up requirement specialized equipment, should make this be adopted non-carbohydrate specialists. report further highlights efficacy prepare several bioactive motifs, such blood type A-type V VI antigens, heparin sulfate disaccharide repeating unit, aminooxy glycosides, α-GalNAc-Serine conjugate, which cannot achieved high yield α-selectivity utilizing Ni(4-F-PhCN)4(OTf)2 catalyst. newly-developed protocol eliminates need synthesis scalable reproducible. Furthermore, computational simulations combination 1H NMR studies analyzed effects various solvents on intramolecular hydrogen bonding network tumor-associated mucin Fmoc-protected GalNAc-threonine amino acid antigen derivative, verifying discrepancies found were unreported.