m-Chloroperbenzoic acid → HCID 15460405, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of phenyl 3-azido-4-O-benzoyl-3,6-di-deoxy-2-O-pivaloyl-1-thio-β-L-galactopyranoside (β-19) (270 mg, 0.575 mmol) in 10 mL of CH2Cl2 at -78° C. is added a solution of mCPBA (159 mg of 64% material, 0.920 mmol) in 2 mL of CH2Cl2. The reaction mixture is allowed to warm to -20° C. and then quenched with TEA (500 μL, 3.59 mmol). The reaction mixture is diluted with 10 mL of CH2Cl2. washed with saturated NaHSO3 (10 mL), saturated NaHCO3 (10 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (60% EtOAc/petroleum ether) to give 231 mg (83%) of 3-azido-4-O-benzoyl1,3,6-tri-deoxy-2-O-pivaloyl-1-(phenylsulfinyl)-β-L-galactopyranose (β-20) as a mixture of diastereomers: Rf 0.26 (50% EtOAc/petroleum ether).

Provenance & Evidence