تفاعل #93695

ord-91d96e7f9f5f4930bc6681db0aea5d9e

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

Cc1ccccc1
toluene

ظروف التفاعل

درجة الحرارة
80°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةAfter cooling
  2. 2
    غسيلthe mixture is washed with water and saturated sodium chloride solution
  3. 3
    أخرىdried
  4. 4
    أخرىevaporated under vacuum

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04614616uspto-grants-1986_09