反应详情

温度

-15 °C

To a solution of phenyl 6-deoxy-2,3,4-tri-O-pivaloyl-1-thio-β-L-galactopyranoside 4 (2.47 g, 5.22 mmol) in 65 mL of CH2Cl2 at -78° C. is added mCPBA (1.53 g, 8.84 mmol). The reaction mixture is allowed to warm to -15° C. and then quenched with methyl sulfide (5.3 mL, 4.48 g, 17.4 mmol) and allowed to warm to room temperature. The reaction mixture is then diluted with 50 mL CH2Cl2, extracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL), dried over Na2SO4, filtered and concentrated to afford a white solid. The sulfoxide is purified using flash chromatography (15% EtOAc/petroleum ether) to afford 1.81 g (66%) of 1,6-dideoxy-2,3,4-tri-O-pivaloyl-1-(phenylsulfinyl)-β-L-galactopyranose 5 as a mixture of diastereomers: Rf 0.05 and 0.13 (15% EtOAc/petroleum ether).

1. temperatureto warm to room temperature
2. extractionextracted with H2O (100 mL), saturated NaHCO3 (100 mL), saturated NaCl (100 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto afford a white solid
7. customThe sulfoxide is purified