反应 #586161

ord-ec7c2000959f40388bf0ce38b2e60689

反应方程式

COc1ccc([C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)cc3O2)cc1O
neohesperidin
COc1ccc([C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)cc3O2)cc1O
Neohesperidin
O=C(CCc1ccccc1)c1ccccc1O
dihydrochalcone
COc1ccc(CCC(O)c2c(O)cc(O)cc2O)cc1O
1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol

溶剂

反应条件

温度
80°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted with ethyl acetate (3×10 ml)
  2. 2
    其他evaporated
  3. 3
    其他to remove ethyl acetate
  4. 4
    workup.DISSOLUTIONdissolved in 1-propanol (5 ml)
  5. 5
    workup.ADDITIONSodium borohydride (25 mg) was added to the propanol solution
  6. 6
    其他After the completion of the reaction
  7. 7
    其他the mixture was separated on a pre-packed C18 column
  8. 8
    洗涤eluting with a MeOH/H2O gradient

实验过程

Neohesperidin is a glycoside of dihydrochalcone. A total weight of 100 mg of neohesperidin was suspended in 10 ml of 1N HCl and heated at 80° C. for 2 hours. The hydrolyzed product (10) was cooled down and extracted with ethyl acetate (3×10 ml). The ethyl acetate layers were combined, evaporated to remove ethyl acetate and dissolved in 1-propanol (5 ml). Sodium borohydride (25 mg) was added to the propanol solution and stirred at room temperature for 2 hours. After the completion of the reaction, the mixture was separated on a pre-packed C18 column eluting with a MeOH/H2O gradient to provide 1-(2,4,6-trihydroxyphenyl)-3-(3′-hydroxy-4′-methoxyphenyl)-1-propanol (11).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07767661B2uspto-grants-2010_08