Triacetoxyperiodinane → (1R,3R,4R,5S)-3,4-dibenzyloxy-1-[(tert-butyl(dimethyl)silyl)oxymethyl]-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (1R,2S,3S,4R,5S)-3,4-dibenzyloxy-1-[(tert-butyl(dimethyl) silyl)oxymethyl]-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-2-ol 28e (15.9 g, 21.7 mmol) in dichloromethane (40 mL) was added Dess-Martin periodinane (18.4 g, 43.5 mmol) at 0° C. The mixture was stirred at 0° C. for 3 hours and adjusted with saturated aqueous sodium bicarnonate till pH becomes 7. The resulting mixture was extracted with dichloromethane (100 mL×2). The combined organic phases were washed with saturated aqueous sodium chloride (100 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 28f as colorless oil (15.9 g, 100%). The crude product was used for next step without further purification.

Provenance & Evidence