Реакция #93695

ord-91d96e7f9f5f4930bc6681db0aea5d9e

Уравнение реакции

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

Реактанты

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

Реагенты

Нет

Растворители

Cc1ccccc1
toluene

Условия реакции

Температура
80°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураAfter cooling
  2. 2
    Промывкаthe mixture is washed with water and saturated sodium chloride solution
  3. 3
    Другоеdried
  4. 4
    Другоеevaporated under vacuum

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04614616uspto-grants-1986_09