Triacetoxyperiodinane → HCID 57857023, compound

Participants

Reaction Steps

To a solution consisting of (Z)-7-((1R,2R,3R,5S)-2-((3R,E)-3-(benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (intermediate 32, 0.191 g, 0.327 mmol) in anhydrous DCM (3 mL) was added Dess-Martin periodinane (0.153, 0.360 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and purified on an 8-g Analogix flash silica cartridge. Elution with 200:1 DCM-methanol with 0.5% acetic acid (300 mL) afforded the title intermediate 33 (208 mg); MS (+cAPCI) m/z 605 (m+Na+).

Provenance & Evidence