反应 #93695

ord-91d96e7f9f5f4930bc6681db0aea5d9e

反应方程式

C[C@]12CC[C@H](O[Si](Cc3ccccc3)(Cc3ccccc3)Cc3ccccc3)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one
CC(C)(C)OO
tert.-butyl hydroperoxide
→
C[C@]12CC[C@H]3[C@@H]([C@@H](O)[C@H]4O[C@]45C[C@@H](O[Si](Cc4ccccc4)(Cc4ccccc4)Cc4ccccc4)CC[C@]35C)[C@@H]1[C@@H]1C[C@@H]1C2=O
3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one

反应物

C[C@]12CC[C@H](O[Si](Cc3ccccc3)(Cc3ccccc3)Cc3ccccc3)CC1=C[C@H](O)[C@H]1[C@@H]3[C@@H]4C[C@@H]4C(=O)[C@@]3(C)CC[C@@H]12
3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one
—
vanadium(IV) oxide acetylacetonate
CC(C)(C)OO
tert.-butyl hydroperoxide

试剂

无

溶剂

Cc1ccccc1
toluene

反应条件

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

后处理

  1. 1
    温度After cooling
  2. 2
    洗涤the mixture is washed with water and saturated sodium chloride solution
  3. 3
    其他dried
  4. 4
    其他evaporated under vacuum

实验过程

24 g of 3β-tribenzylsilyloxy-7β-hydroxy-15β,16β-methylene-5-androsten-17-one is dissolved in 50 ml of toluene, combined with 500 mg of vanadium(IV) oxide acetylacetonate, and heated to 80° C. A solution of 75 ml tert.-butyl hydroperoxide (10 ml 80% tert.-butyl hydroperoxide in 100 ml of toluene) is added dropwise to the reaction mixture, and the latter is allowed to stand for 1.5 hours at this temperature. After cooling, the mixture is washed with water and saturated sodium chloride solution, dried, and evaporated under vacuum, thus obtaining 24.5 g of 3β-tribenzylsilyloxy-5,6β-epoxy-7β-hydroxy-15β,16β-methylene-5β-androstan-17-one.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US04614616uspto-grants-1986_09