Reacción #48116

Ecuación de reacción

Hydrogen peroxide

4-(β-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile

→

4-(β-D-glucopyranos-1-yl)-2-(4-methylsulfinyl-benzyl)-benzonitrile

Disolventes

water

1,1,1,3,3,3-hexafluoroisopropanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution
2. 2
   OtroThe organic phase is separated
3. 3
   Extracciónthe aqueous phase is extracted with ethyl acetate
4. 4
   SecadoThe combined organic phases are dried over sodium sulfate
5. 5
   Otrothe solvent is removed
6. 6
   OtroThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1)

Procedimiento

35% Hydrogen peroxide in water (48 μL) is added to 4-(β-D-glucopyranos-1-yl)-2-(4-methylsulfanyl-benzyl)-benzonitrile (83 mg) in 1,1,1,3,3,3-hexafluoroisopropanol (2 mL). The resulting solution is stirred at ambient temperature for 1 h and then quenched by the addition of aqueous Na2S2O3 solution and aqueous NaHCO3 solution. The organic phase is separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->5:1).

Fuente