反応式
CC[O:3][CH2:4][CH3:5].[Li].[Cl-].[NH4+].O[C@H]1CC[C@@:25]2([CH3:28])[C:12](=[CH:13][C@H:14](C=C)[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:29])C1.N.[O:33]1CC[CH2:35][CH2:34]1>>[OH:33][C@@H:34]1[C@@:25]2([CH3:28])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:29])[CH2:5][C@@H:4]([OH:3])[CH2:35]1参加物
6
実験手順
Alkaline hydrogen peroxide epoxidation of androsta-1,4,6-triene-3,17-dione 17-ketal 1 with basic hydrogen peroxide yields the 1α,2α-epoxide 2. Treatment of 1α,2α-epoxyandrosta-4,6-dien-3,17-dione 17-ketal 2 with a large excess each of lithium metal and ammonium chloride in ammonia-tetrahydrofuran (1:1) under reflux leads to 1α,3β-dihydroxyandrost-5-en-17-one 17-ketal 3. Hydrolysis of the ketal affords 1α,3β-dihydroxyandrost-5-en-17-one, 4. Also, fermentation of DHEA with penicillium aspergillus affords 4, i.e. penicillium aspergillus may be able to 1α-hydroxylate other substrates. ##STR31## Dodson, R. M., Goldkamp, A. M., and Muir, R. D., JACS, 1957, 79, 3921. Dodson, R. M., Goldkamp, A. M., and Muir, R. D., JACS, 1960, 82, 4026.
出典と根拠
- ORDレコード
- ord-fa243eefd18043779c57df25f4d94658
- 出典データセット
- uspto-grants-1998_02
- 特許番号
- US05714481
関連ノート
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