Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Diethyl Ether → 1-Hydroxydehydroepiandrosterone
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Diethyl Ether | HCID 3283 | — |
| 반응물 | Ammonium Chloride | HCID 25517 | — |
| 반응물 | Lithium | HCID 3028194 | — |
| 반응물 | Ammonia tetrahydrofuran | HCID 21982362 | — |
| 반응물 | 3beta-Hydroxy-7beta-ethenyl-5-androsten-17-one | HCID 67648341 | — |
| 생성물 | 1-Hydroxydehydroepiandrosterone | HCID 167955 | — |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05714481 |
| 출처 데이터셋 | uspto-grants-1998_02 |
| ORD ID | ord-fa243eefd18043779c57df25f4d94658 |
| 출처 메모 | uspto-grants-1998_02 |