ES251876A1 - New compounds useful in steroid synthesis and processes for the preparation thereof - Google Patents
New compounds useful in steroid synthesis and processes for the preparation thereofInfo
- Publication number
- ES251876A1 ES251876A1 ES0251876A ES251876A ES251876A1 ES 251876 A1 ES251876 A1 ES 251876A1 ES 0251876 A ES0251876 A ES 0251876A ES 251876 A ES251876 A ES 251876A ES 251876 A1 ES251876 A1 ES 251876A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- acid
- diacyloxy
- seco
- hydroxy
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises the 18,11-lactones of 11b -hydroxy-13,17-secoetiocholan-17,18-dioic acids of the general formula <FORM:0922315/IV(a)/1> wherein R represents =O, or b -OH, a -H, the methyl ester of 3a -hydroxy-11-keto-13,17-seco-etiochol-12-en-17-oic acid of the formula <FORM:0922315/IV(a)/2> the 17,18-lactone of 3a ,11b -diacyloxy-18-hydroxy-13,17-seco-13a -etiocholan-17-oic acid of the formula <FORM:0922315/IV(a)/3> and 3a ,11b - diacyloxy-13,17- seco-etiocholan-17,18-dioic acid of the formula <FORM:0922315/IV(a)/4> and the preparation of a compound of the first formula wherein R represents b -OH, a -H (1) by treating 3a , 11b -dihydroxy-17-keto-17ahydroxymethylene- 18-nor-D-homo-13a -etiocholane of the formula <FORM:0922315/IV(a)/5> with alkaline hydrogen peroxide, and (2) by treating 3a ,11b -diacyloxy-17 -keto-18-nor-D-homo-13a -etiocholane of the formula <FORM:0922315/IV(a)/6> (which may be prepared by acylating the corresponding free 3a ,11b -dihydroxy compound) with an organic per-acid to form the 17,18-lactone of 3a ,11b -diacyloxy-18-hydroxy-13,17-seco-13a -etiocholan-17-oic acid of the third formula above, oxidising this lactone with a mixture of chromic and sulphuric acids to form 3a ,11b -diacyloxy-13,17-seco-etiocholan-17,18-dioic acid of the fourth formula above, and treating this compound with warm alkali and then acidifying, wherein in the above processes (1) and (2) the initial reactant is prepared from 3a -hydroxy-11-keto-13,17-secoetiochol-12-en-17-oic acid or the methyl ester thereof obtainable by esterifying the acid, e.g. by reacting the acid with a mixture of sulphuric acid and methanol and which has the second formula above, by a process described in Specification 922,316.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR776718 | 1958-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES251876A1 true ES251876A1 (en) | 1960-01-01 |
Family
ID=8707738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0251876A Expired ES251876A1 (en) | 1958-10-15 | 1959-09-03 | New compounds useful in steroid synthesis and processes for the preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE583615A (en) |
| CH (2) | CH417581A (en) |
| ES (1) | ES251876A1 (en) |
| GB (2) | GB922315A (en) |
| SE (1) | SE302300B (en) |
-
1959
- 1959-09-01 GB GB2978459A patent/GB922315A/en not_active Expired
- 1959-09-01 GB GB680762A patent/GB922316A/en not_active Expired
- 1959-09-03 ES ES0251876A patent/ES251876A1/en not_active Expired
- 1959-09-09 CH CH9996559A patent/CH417581A/en unknown
- 1959-09-09 CH CH7801559A patent/CH406199A/en unknown
- 1959-10-14 BE BE583615A patent/BE583615A/en unknown
-
1963
- 1963-12-10 SE SE1372663A patent/SE302300B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE302300B (en) | 1968-07-15 |
| BE583615A (en) | 1969-04-14 |
| CH406199A (en) | 1966-01-31 |
| CH417581A (en) | 1966-07-31 |
| GB922315A (en) | 1963-03-27 |
| GB922316A (en) | 1963-03-27 |
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