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Diethyl Ether → 1-Hydroxydehydroepiandrosterone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diethyl Ether | HCID 3283 | — |
| 反応物 | Ammonium Chloride | HCID 25517 | — |
| 反応物 | Lithium | HCID 3028194 | — |
| 反応物 | Ammonia tetrahydrofuran | HCID 21982362 | — |
| 反応物 | 3beta-Hydroxy-7beta-ethenyl-5-androsten-17-one | HCID 67648341 | — |
| 生成物 | 1-Hydroxydehydroepiandrosterone | HCID 167955 | — |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05714481 |
| 出典データセット | uspto-grants-1998_02 |
| ORD ID | ord-fa243eefd18043779c57df25f4d94658 |
| 出典メモ | uspto-grants-1998_02 |