Sodium Thiosulfate → HCID 57515882, compound

Participants

Reaction Steps

To a solution of tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-1-hydroxy-6-(trimethylsilyl)hex-5-yn-3-ylcarbamate (1.83 g, 4.4 mmol) in DCM (20 mL) were added sodium bicarbonate (1.5 g, 18 mmol) and Dess-MartinPeriodinane (2.4 g, 5.7 mmol) and the reaction was stirred at rt for 1 h. The mixture was quenched with sat NaHCO3 followed by the addition of sodium thiosulfate (3.5 g, 22 mmol) and stirred for an additional 1 h. The reaction was extracted with DCM and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated to afford a light yellow oil as tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-1-oxo-6-(trimethylsilyl)hex-5-yn-3-ylcarbamate. MS m/z: 316.2 (M+1).

Provenance & Evidence