Triacetoxyperiodinane → HCID 69814972, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2R and 2S)-3-[4-[3-(tert-butyldiphenysilyloxy)propyl]phenoxy]-1-[4-(tert-butoxycarbonyl)phenoxy]-3-methyl-2-butanol (0.60 g, 0.89 mmol) in dry dichloromethane (30 ml) was treated with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (1.50 g, 3.57 mmol) and the resulting mixture was stirred at 22° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with 5% sodium thiosulfate, saturated sodium bicarbonate and brine. After drying (magnesium sulfate), the organic phase was concentrated and chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (98:2) gave 0.587 g (98%) of the title material as a clear oil.

Provenance & Evidence