反应 #1755509

ord-83b5fa827da743ce920aaff833263d6a

反应方程式

Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1
3-(β-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole
O=C(OCc1ccccc1)ON1C(=O)CCC1=O
N-(benzyloxycarbonyloxy)-succinimide
Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(=O)OCc1ccccc1
1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole
收率 75.3%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度the mixture was heated
  2. 2
    温度under reflux overnight
  3. 3
    浓缩The reaction mixture was concentrated under reduced pressure
  4. 4
    其他the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

实验过程

To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-iso-propoxyphenyl)methyl]-5-methyl-1H-pyrazole (1.3 g) in tetrahydrofuran (30 mL) was added N-(benzyloxycarbonyloxy)-succinimide (1.6 g), and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (1.3 g).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07989424B2uspto-grants-2011_08