Water → HCID 57723947, compound

Participants

Reaction Steps

To a solution of optically pure (4aR,8aS-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (50 mg, 0.29 mmol) in 4.5 mL of THF-tert-BuOH—H2O (1:3:0.5) was added NMO (45 mg, 0.32 mmol) and the solution was stirred for 5 min. at ambient temperature. OsO4 (15 μL, 25 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 4 days. Sodiumhydrosulphite (0.2 g), Florisil (2.0 g) and H2O (5 ml) were added and the mixture was stirred for 30 min, wash with acetone (100 mL), filtered through filter paper and extracted with EtOAc (80 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

Provenance & Evidence