Reacción #48115

Ecuación de reacción

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile

pentafluoroethyltrimethylsilane

KF

NaHCO3

→

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe resulting mixture is extracted with ethyl acetate
2. 2
   SecadoThe combined organic phases are dried over sodium sulfate
3. 3
   Otrothe solvent is removed
4. 4
   workup.DISSOLUTIONThe residue is dissolved in methanol (8 mL)
5. 5
   workup.ADDITIONtreated with 4 M KOH solution (0.8 mL)
6. 6
   workup.ADDITIONdiluted with aqueous NaHCO3 solution
7. 7
   OtroAfter removal of the methanol under reduced pressure
8. 8
   Extracciónthe residue is extracted with ethyl acetate
9. 9
   Otrothe combined organic extracts are dried
10. 10
    Otrothe solvent is removed
11. 11
    OtroThe residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

Procedimiento

A flask charged with 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-(4-iodo-benzyl)-benzonitrile (0.16 g), pentafluoroethyltrimethylsilane (0.14 g), KF (43 mg), CuI (0.16 g), DMF (2 mL) and Ar atmosphere is heated at 60° C. for 24 h. Then, aqueous NaHCO3 solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is dissolved in methanol (8 mL) and treated with 4 M KOH solution (0.8 mL). The solution is stirred at room temperature for 1 h and then diluted with aqueous NaHCO3 solution. After removal of the methanol under reduced pressure, the residue is extracted with ethyl acetate, the combined organic extracts are dried and the solvent is removed. The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1).

Fuente