Hydrogen Peroxide → HCID 11984447, compound

Participants

Reaction Conditions

Reaction Steps

To a solution containing 52.53 g (0.115 mol) of tert-butyl (5S)-6-tert-butyldiphenylsilyloxy-5-hydroxy-3-oxohexanoate, 800 ml of anhydrous tetrahydrofuran and 200 ml of anhydrous methanol was added 126 ml (0.126 mol) of a 1 M solution of diethyl methoxy borane in tetrahydrofuran with stirring at -70° C. After stirring the mixture for 1 hour at -65° C., thereto was added 5.66 g (0.15 mol) of sodium borohydride and the mixture was reacted for 4 hours at the same temperature. The reactant was added dropwise to the mixture of 425 ml of 30% hydrogen peroxide, 850 ml of 0.2 M phosphate buffer solution (pH 7.0 ) and 850 ml of methanol at -20° to -10° C. Further after stirring the mixture for a half hour at room temperature, the mixture was concentrated under reduced pressure. The concentrated solution was extracted with methylene chloride, and the methylene chloride layer was washed with water, then dried and distilled away under reduced pressure. The residue was purified by subjecting to silica gel column chromatography [eluent: methylene chloride-ethyl acetate (10:1)]to give 40.1 g of tert-butyl (3R,5S)-6-tert-butyldiphenylsilyloxy-3,5-dihydroxyhexanoate as syrups (yield: 75%).

Provenance & Evidence