tert-Butyl hydroperoxide → 3beta-Tribenzylsilyloxy-5,6beta-epoxy-7beta-hydroxy-15beta,16beta-methylene-5beta-androstan-17-one

HRID 65417

反応式

[CH2:1]([Si:8]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][C@H:14]([OH:31])[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:50]O)(C)(C)C>C1(C)C=CC=CC=1>[CH2:39]([Si:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:12]3([O:50][C@@H:13]3[C@H:14]([OH:31])[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:30][C@@H:18]3[C:19]2=[O:29])[CH2:11]1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

参加物

反応条件

温度: 80 °C

実験手順

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.

後処理

temperatureAfter cooling
washthe mixture is washed with water and saturated sodium chloride solution
customdried
customevaporated under vacuum

出典と根拠

ORDレコード: ord-91d96e7f9f5f4930bc6681db0aea5d9e
出典データセット: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04614616

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート