1: hydrogen; palladium on activated charcoal / methanol / 15 h 2: triphenylphosphine; carbon tetrabromide / dichloromethane / 1 h / 20 °C 3: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C 4: hydrogen; palladium on activated charcoal / ethyl acetate 5: potassium carbonate; water / methanol / 12 h View Scheme

With  (DHQ)2PHAL; methanesulfonamide; H6O6Os(2-)*2K(1+); potassium carbonate; potassium hexacyanoferrate(III) in  water; tert-butyl alcohol T=0°C; Sharpless Dihydroxylation; 24 h;  Show Experimental Procedure