Sodium Dithionite → HCID 12179948, compound

Participants

Reaction Steps

To (2S,3R)-3-acetoxy-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (200 mg, 0.93 mmol) in 18 ml of THF-tert-BuOH—H2O (4:11.8:2) was added NMO (408 mg, 2.98 mmol) and the solution was stirred for 5 min at ambient temperature. OsO4 (0.2 ml, 2.5 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 72 H. Sodium hydrosulphite (0.83 g), Florisil (2.0 g) and H2O (2 ml) were added sequentially and the mixture was stirred for 30 minutes, washed with 200 ml EtOAc, filtered through filter paper and the solvent was evaporated. The crude product was purified by flash chromatography with 20-80% EtOAc-hexane to give (2S,3R,4S,5S)-3-acetoxy-4,5-dihydroxy-tetrahydropyran-2-carboxylic acid ethyl ester

Provenance & Evidence