m-Chloroperbenzoic acid → HCID 15460414, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl 2-azido-3,4-di-O-acetyl-2,6-dideoxy-1-thio-L-galactopyranoside (22) (1.02 g, 2.80 mmol) in 50 mL of CH2Cl2 is added NaHCO3 at room temperature. The reaction mixture is cooled to -78° C., and mCPBA (0.878 g, 2.80 mmol, 50-60%) is added. The reaction mixture is stirred at -78° C. for 30 minutes and then allowed to warm to -40° C. over 1 h. The reaction is quenched with dimethyl sulfide (1 mL) at -40° C. and then poured into a solution of saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (3×30 mL) The organic layers are combined, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography (EtOAc/petroleum ether) to afford the title compound 26 as a mixture of diastereomers.

Provenance & Evidence