JPS5581899A - Mutual conversion between hydroxycholesterol stereoisomers - Google Patents
Mutual conversion between hydroxycholesterol stereoisomersInfo
- Publication number
- JPS5581899A JPS5581899A JP15411178A JP15411178A JPS5581899A JP S5581899 A JPS5581899 A JP S5581899A JP 15411178 A JP15411178 A JP 15411178A JP 15411178 A JP15411178 A JP 15411178A JP S5581899 A JPS5581899 A JP S5581899A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxyl
- hydroxycholesterol
- acyl
- stereoisomers
- 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.)
- Granted
Links
- IXRAQYMAEVFORF-UTLNTRLCSA-N (3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol Chemical class C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(O)[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 IXRAQYMAEVFORF-UTLNTRLCSA-N 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000002252 acyl group Chemical group 0.000 abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001033 ether group Chemical group 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 benzoic acid Chemical class 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RUHCATDGSSLXPZ-UHFFFAOYSA-N dicarboxyazaniumylideneazanide Chemical compound OC(=O)[N+](=[N-])C(O)=O RUHCATDGSSLXPZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
PURPOSE: To obtain a compound useful as an intermediate for the synthesis of medicines, by esterifying and isomerizing one of the stereoisomers of hydroxycholesterol in the presence of a diazodicarboxylic acid and a phosphine.
CONSTITUTION: (A) A hydroxycholesterol of formula I: (R1 is acyl or a group forming an ether group with a hydroxyl group, etc.; R2 is H, hydroxyl, acyl, or a hydroxyl group protected by a group forming an ether group with a hydroxyl group) is reacted with (B) a diazodicarboxylic dialkyl ester of formula II: (R3 is alkyl group) in the presence of (C) a triarylphosphine, in (D) a solvent, e.g. an organic carboxylic acid, e.g. benzoic acid, and tetrahydrofuran at room temperature to isomerize and esterify the hydroxyl group linked to the asymmetric carbon atom at the 24-position. The acyl group is hydrolyzed to eliminate the hydroxyl-protecting group, if necessary.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15411178A JPS5581899A (en) | 1978-12-15 | 1978-12-15 | Mutual conversion between hydroxycholesterol stereoisomers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15411178A JPS5581899A (en) | 1978-12-15 | 1978-12-15 | Mutual conversion between hydroxycholesterol stereoisomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5581899A true JPS5581899A (en) | 1980-06-20 |
| JPS629118B2 JPS629118B2 (en) | 1987-02-26 |
Family
ID=15577157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15411178A Granted JPS5581899A (en) | 1978-12-15 | 1978-12-15 | Mutual conversion between hydroxycholesterol stereoisomers |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5581899A (en) |
-
1978
- 1978-12-15 JP JP15411178A patent/JPS5581899A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| TETRAHEDRON LETTERS=1973 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS629118B2 (en) | 1987-02-26 |
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