反応 #48115

反応方程式

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

溶媒

DMF

反応条件

後処理

1. 1
   抽出the resulting mixture is extracted with ethyl acetate
2. 2
   乾燥The combined organic phases are dried over sodium sulfate
3. 3
   その他the 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
   その他After removal of the methanol under reduced pressure
8. 8
   抽出the residue is extracted with ethyl acetate
9. 9
   その他the combined organic extracts are dried
10. 10
    その他the solvent is removed
11. 11
    その他The residue is chromatographed on silica gel (dichloromethane/methanol 1:0->8:1)

実験手順

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).

出典