Synthesis of Biologically Relevant β-N-Glycosides by Biphasic Epoxidation-Aminolysis of D-Glycals

Abstract

Several β-N-glycosides were obtained upon a simple and efficient two-step methodology. First, α-1,2-anhydrosugars were prepared diastereoselectively by the oxidation of 3,4,6-tri-O-benzyl-D-glucal under biphasic conditions (CH2Cl2/water) using dimetyldioxirane (DMDO) generated in situ from oxone/acetone mixture and amphiphilic imidazolium ionic liquid (DodMImBF4) as phase transfer catalyst. Immediately, β-N-glycosides were synthesized in good yields by aminolysis of these α-1,2-anhydrosugars using CH3CN as solvent. The overall process allows stereoselective generation of biologically relevant carbohydrate derivatives.