반응 #48115

반응 방정식

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

용매

DMF

반응 조건

후처리

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

실험 절차

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).

출처