Triacetoxyperiodinane → HCID 59235323, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) stirred suspension of Dess-Martin periodinane (1.24 g, 2.92 mmol) in dichloromethane (20 mL) was added (5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (1.76 g, 2.25 mmol) (prepared as described in U.S. Ser. No. 12/060,767) in dichloromethane (3 mL). The mixture was stirred for 2 hours at 0° C., and the reaction was quenched with 2N sodium hydroxide (5 mL). The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate, then with water and then with brine, and then dried over anhydrous sodium sulfate. The combined filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give 0.87 g of white solid. MS ESI+ (m/z): 798 (M+18)+.

Provenance & Evidence