반응 #93695

ord-91d96e7f9f5f4930bc6681db0aea5d9e

반응 방정식

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

반응물

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

시약

없음

용매

Cc1ccccc1
toluene

반응 조건

온도
80°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도After cooling
  2. 2
    세척the mixture is washed with water and saturated sodium chloride solution
  3. 3
    기타dried
  4. 4
    기타evaporated under vacuum

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04614616uspto-grants-1986_09