GB467161A - Process for the manufacture of derivatives of 3.17-diols-of the cyclopentano polyhydrophenanthrene series - Google Patents
Process for the manufacture of derivatives of 3.17-diols-of the cyclopentano polyhydrophenanthrene seriesInfo
- Publication number
- GB467161A GB467161A GB2509435A GB2509435A GB467161A GB 467161 A GB467161 A GB 467161A GB 2509435 A GB2509435 A GB 2509435A GB 2509435 A GB2509435 A GB 2509435A GB 467161 A GB467161 A GB 467161A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- derivatives
- acid
- androstendiol
- substituent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Landscapes
- Mechanical Treatment Of Semiconductor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
17 - Mono - derivatives of 3 : 17-diols of the cyclopentanopolyhydrophenanthrene series are obtained by subjecting di-derivatives of the above diols other than di-esters in which the 3-(OH) group is replaced by a substituent which is relatively easily hydrolyzable and the 17-(OH) group is replaced by a substituent which is relatively difficultly hydrolyzable, to a hydrolysis in which the substituent on the carbon atom 3 is converted into the hydroxyl group, while the substituent on the carbon atom 17 is left substantially unaffected. Suitable mixed di-derivatives can be obtained by treating selected 3-mono-derivatives prepared for example by reducing derivatives of corresponding 3-hydroxy-17-keto compounds with esterifying, etherifying, or halogenating agents. As examples of substituents which are easily reconvertable into the hydroxy group on hydrolysis there are mentioned aliphatic carboxylic acid radicals having a straight chain of carbon atoms, such as acetic acid. As examples of more difficultly hydrolyzable groups there are mentioned acylating agents with branched chains, such as compounds of iso-butyric acid, iso-valeric acid, substituted and unsubstituted benzoic and naphthoic acids, chlorsulphonic acids, chloroformic acid, and phenylisocyanic acid. In examples: (1) Androstendiol - 3 : 17 - monotriphenylmethyl ether-3 obtained from dehydroandrosterone - triphenylmethyl ether by reduction, is acetylated with acetic anhydride and hydrolyzed with N-sulphuric acid to yield the 17-monoacetate of androstendiol-3 : 17; (2) androstendiol - 3 : 17 - monoacetate - 3 obtained by hydrogenating dehydroandrosterone acetate is converted into androstendiol - 3 : 17 - monoacetate - 3 - triphenylmethyl ether - 17 by treatment with triphenylmethyl chloride, and hydrolyzed to the 17 - triphenylmethyl ether of androstandiol - 3 : 17. Instead of triphenylmethyl ether these may be used in the above examples the diphenylmethyl ether, the p-toluyl - diphenylmethyl ether, or the methoxy - methyl ether; (3) 3 - acetoxy-17-chlorandrosten is hydrolyzed in methyl alcoholic potassium hydroxide to give 3-hydroxy-17-chlor-androsten. Specification 464,396 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2509435A GB467161A (en) | 1935-09-09 | 1935-09-09 | Process for the manufacture of derivatives of 3.17-diols-of the cyclopentano polyhydrophenanthrene series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2509435A GB467161A (en) | 1935-09-09 | 1935-09-09 | Process for the manufacture of derivatives of 3.17-diols-of the cyclopentano polyhydrophenanthrene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB467161A true GB467161A (en) | 1937-06-09 |
Family
ID=10222122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2509435A Expired GB467161A (en) | 1935-09-09 | 1935-09-09 | Process for the manufacture of derivatives of 3.17-diols-of the cyclopentano polyhydrophenanthrene series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB467161A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE860215C (en) * | 1941-07-21 | 1952-12-18 | Ciba Geigy | Process for the preparation of phosphoric acid esters of germ gland hormone-active polyoxy compounds |
-
1935
- 1935-09-09 GB GB2509435A patent/GB467161A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE860215C (en) * | 1941-07-21 | 1952-12-18 | Ciba Geigy | Process for the preparation of phosphoric acid esters of germ gland hormone-active polyoxy compounds |
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