反应 #1755493

ord-5e7d845fcabf4f069a615a71f51294a8

反应方程式

Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1
1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one
CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
acetobromo-α-D-glucose
CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
4-[(4-isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole
收率 39.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他at 65° C.
  2. 2
    其他overnight
  3. 3
    其他The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)
  4. 4
    其他Further purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1)

实验过程

To a suspension of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4 A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred under shading the light at 65° C. overnight. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran). Further purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) afforded 4-[(4-isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).

来源

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