Ruthenium(III) Chloride Hydrate

Typical Procedure:
To a stirred solution of glycal (1.0 eq.) and N-nucleophile (1.2 eq.) in anhydrous acetonitrile (2 mL/mmol) under an atmosphere of argon is added RuCl₃ (5 mol%) at room temperature. The reaction mixture is stirred until the complete consumption of the glycal as indicated by TLC. The reaction mixture is concentrated in vacuo, the crude residue is re-dissolved in dichloromethane and loaded on a silica gel column. The product is purified by silica gel chromatography using hexane/EtOAc to afford the 2,3-unsaturated-N-glycosides as an inseparable α/β mixture or α-anomer.