2-Iodoxybenzoic acid → (1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2,2-trifluoro ethoxy)phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octane-1-carbaldehyde

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Reaction Steps

To a solution of [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[[4-(2,2,2-trifluoroethoxyl) phenyl]methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 171 (2.3 g, 3.02 mmol) in dichloromethane (100 mL) was added 2-iodoxybenzoic acid (1.70 g, 6.04 mmol) at room temperature. The mixture was refluxed for 20 hours, then cooled to room temperature and filtered. The filtrate was washed with saturated aqueous sodium chloride (50 mL) and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 17m as pale yellow viscous oil (1.85 g, 80.4%, HPLC: 76.76%). This material was not further purified.

Provenance & Evidence