反应详情

To a suspension of 4-[(4-methylthiophenyl)methyl]-5-phenyl-1,2-dihydro-3H-pyrazole-3-one (0.087 g), acetobromo-α-D-glucose (0.62 g) and benzyltri(n-butyl)ammonium bromide (0.054 g) in dichloromethane (3 mL) was added a sodium hydroxide aqueous solution (5 mol/L, 0.9 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). The obtained semi purified 4-[(4-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-1H-pyrazole was dissolved in methanol (5 mL), and sodium methoxide (28% methanol solution, 0.28 mL) was added to the solution. The mixture was stirred at room temperature for 2 hours. Acetic acid (0.090 g) was added to the reaction mixture, and the solvent was removed. Water (5 mL) was added to the residue, and the mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol). Column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification to give the title compound (0.033 g).

1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
2. customThe obtained semi purified 4-[(4-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-1H-pyrazole
3. dissolutionwas dissolved in methanol (5 mL)
4. additionsodium methoxide (28% methanol solution, 0.28 mL) was added to the solution
5. stirringThe mixture was stirred at room temperature for 2 hours
6. additionAcetic acid (0.090 g) was added to the reaction mixture
7. customthe solvent was removed
8. additionWater (5 mL) was added to the residue
9. customthe mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol)
10. customColumn chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification