Hydrochloric Acid → (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carboxylic acid

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Reaction Conditions

Reaction Steps

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 25l (0.45 g, 0.58 mmol) in tetrahydrofuran (20 mL) was added sodium bicarbonate (0.49 g, 5.8 mmol) at room temperature, and then potassium bromide (6.9 mg, 0.06 mmol), 2,2,6,6-tetramethylpiperidinooxy (9 mg, 0.06 mmol) and sodium hypochlorite (9 mL, available chlorine ≧5.5%) were added in turn at 0° C. The mixture was stirred at 0° C. for 40 min and acidified with aqueous HCl (1 N) till pH becomes 4. The resulting mixture was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with water (20 mL×2) and saturated brine (20 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 25m (0.46 g, 100%) as a white solid. This material was not further purified.

Provenance & Evidence