Triacetoxyperiodinane → HCID 86694563, compound

Participants

Reaction Steps

Dess-martin reagent (390 mg, 0.92 mM) was placed in a 100 ml round bottom flask and 5 ml of methylene chloride was added, 5 min later, methyl 4-{(5R,6S)-5-[(tert-butoxycarbonyl)amino]-6-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-7-phenoxyheptyl}benzoate from step E (360 mg, 0.61 mM) in 5 ml of methylene chloride was added, and the resulting mixture was stirred for 3 h at RT. The mixture was then filtered and the filtrate was washed by saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated to dryness. The residue was then loaded onto a Biotage column (40 S) and eluted with hexane/ethyl acetate (0-30% EA, 500 ml; 30-50% EA, 300 ml) to afford 139 mg of the title compound. LC-MS: m/z (ES) 608.24 (M=23).

Provenance & Evidence