JPS5735597A - 25,26-epoxy-3beta,24-dihydroxycholest-5-ene or its hydroxyl- protected derivative and their preparation - Google Patents
25,26-epoxy-3beta,24-dihydroxycholest-5-ene or its hydroxyl- protected derivative and their preparationInfo
- Publication number
- JPS5735597A JPS5735597A JP11039980A JP11039980A JPS5735597A JP S5735597 A JPS5735597 A JP S5735597A JP 11039980 A JP11039980 A JP 11039980A JP 11039980 A JP11039980 A JP 11039980A JP S5735597 A JPS5735597 A JP S5735597A
- Authority
- JP
- Japan
- Prior art keywords
- ene
- hydroxyl
- epoxy
- dihydroxycholest
- 3beta
- 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
- LRUCPRLVALPSCK-JKKSSRGPSA-N (3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroxy-5-(2-methyloxiran-2-yl)pentan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound O1C(C1)(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O LRUCPRLVALPSCK-JKKSSRGPSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 abstract 1
- 235000005282 vitamin D3 Nutrition 0.000 abstract 1
- 239000011647 vitamin D3 Substances 0.000 abstract 1
- 229940021056 vitamin d3 Drugs 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
Landscapes
- Steroid Compounds (AREA)
Abstract
NEW MATERIAL:25,26-Epoxy-3beta,24-dihydroxycholest-5-ene of formula I (R<1>, R<2> are H, hydroxyl-protecting group) or its hydroxyl-protected derivatives. EXAMPLE:25(S),26-Epoxy-24(R)-hydroxycholest-5-ene. USE:Synthetic intermediate of active-type vitamin D3. 24,25-Dihydroxycholecarciferol or its 24-position epimer is synthesized. PREPARATION:A compound of formula II is epoxidized with t-butylhydroperoxide in the presence of a catalyst and, when needed, hydrolyzed to produce the compound of formula I. The reaction is conducted in a solvent such as benzene at -10-100 deg.C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11039980A JPS5735597A (en) | 1980-08-13 | 1980-08-13 | 25,26-epoxy-3beta,24-dihydroxycholest-5-ene or its hydroxyl- protected derivative and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11039980A JPS5735597A (en) | 1980-08-13 | 1980-08-13 | 25,26-epoxy-3beta,24-dihydroxycholest-5-ene or its hydroxyl- protected derivative and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5735597A true JPS5735597A (en) | 1982-02-26 |
| JPS6246556B2 JPS6246556B2 (en) | 1987-10-02 |
Family
ID=14534812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11039980A Granted JPS5735597A (en) | 1980-08-13 | 1980-08-13 | 25,26-epoxy-3beta,24-dihydroxycholest-5-ene or its hydroxyl- protected derivative and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5735597A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018519329A (en) * | 2015-07-06 | 2018-07-19 | セージ セラピューティクス， インコーポレイテッド | Oxysterols and methods of their use |
| US11104701B2 (en) | 2013-03-13 | 2021-08-31 | Sage Therapeutics, Inc. | Neuroactive steroids and methods of use thereof |
| US11111266B2 (en) | 2016-10-18 | 2021-09-07 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11117924B2 (en) | 2015-07-06 | 2021-09-14 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11149054B2 (en) | 2016-10-18 | 2021-10-19 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11149056B2 (en) | 2016-09-30 | 2021-10-19 | Sage Therapeutics, Inc. | C7 substituted oxysterols and methods of use thereof |
| US11279730B2 (en) | 2016-07-07 | 2022-03-22 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11407782B2 (en) | 2016-05-06 | 2022-08-09 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11884697B2 (en) | 2016-04-01 | 2024-01-30 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US12129275B2 (en) | 2011-09-08 | 2024-10-29 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| US12129276B2 (en) | 2014-06-18 | 2024-10-29 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US12268697B2 (en) | 2015-07-06 | 2025-04-08 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
-
1980
- 1980-08-13 JP JP11039980A patent/JPS5735597A/en active Granted
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12129275B2 (en) | 2011-09-08 | 2024-10-29 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| US11905309B2 (en) | 2013-03-13 | 2024-02-20 | Sage Therapeutics, Inc. | Neuroactive steroids and methods of use thereof |
| US11104701B2 (en) | 2013-03-13 | 2021-08-31 | Sage Therapeutics, Inc. | Neuroactive steroids and methods of use thereof |
| US12129276B2 (en) | 2014-06-18 | 2024-10-29 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11732000B2 (en) | 2015-07-06 | 2023-08-22 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| JP2018519329A (en) * | 2015-07-06 | 2018-07-19 | セージ セラピューティクス， インコーポレイテッド | Oxysterols and methods of their use |
| US12268697B2 (en) | 2015-07-06 | 2025-04-08 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| JP2021063118A (en) * | 2015-07-06 | 2021-04-22 | セージ セラピューティクス， インコーポレイテッド | Oxysterols and methods of use thereof |
| US11117924B2 (en) | 2015-07-06 | 2021-09-14 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11884697B2 (en) | 2016-04-01 | 2024-01-30 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11878995B2 (en) | 2016-05-06 | 2024-01-23 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11407782B2 (en) | 2016-05-06 | 2022-08-09 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11279730B2 (en) | 2016-07-07 | 2022-03-22 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11926646B2 (en) | 2016-09-30 | 2024-03-12 | Sage Therapeutics, Inc. | C7 substituted oxysterols and methods of use thereof |
| US11149056B2 (en) | 2016-09-30 | 2021-10-19 | Sage Therapeutics, Inc. | C7 substituted oxysterols and methods of use thereof |
| US12331070B2 (en) | 2016-09-30 | 2025-06-17 | Sage Therapeutics, Inc. | C7 substituted oxysterols and methods of use thereof |
| US11149054B2 (en) | 2016-10-18 | 2021-10-19 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11613556B2 (en) | 2016-10-18 | 2023-03-28 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US11111266B2 (en) | 2016-10-18 | 2021-09-07 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| US12180247B2 (en) | 2016-10-18 | 2024-12-31 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6246556B2 (en) | 1987-10-02 |
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