JPS5716899A - Production of 24 (r) or 24 (s)-hydroxycholesterol - Google Patents
Production of 24 (r) or 24 (s)-hydroxycholesterolInfo
- Publication number
- JPS5716899A JPS5716899A JP9051980A JP9051980A JPS5716899A JP S5716899 A JPS5716899 A JP S5716899A JP 9051980 A JP9051980 A JP 9051980A JP 9051980 A JP9051980 A JP 9051980A JP S5716899 A JPS5716899 A JP S5716899A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- produce
- optically active
- reaction
- 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
- IOWMKBFJCNLRTC-RNCHBCSGSA-N (24R)-24-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CC2 IOWMKBFJCNLRTC-RNCHBCSGSA-N 0.000 title abstract 2
- IOWMKBFJCNLRTC-XWXSNNQWSA-N (24S)-24-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@H](O)C(C)C)[C@@]1(C)CC2 IOWMKBFJCNLRTC-XWXSNNQWSA-N 0.000 title abstract 2
- IOWMKBFJCNLRTC-UHFFFAOYSA-N 24S-hydroxycholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(O)C(C)C)C1(C)CC2 IOWMKBFJCNLRTC-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- SNOXQOOPUCMFPS-ZLNGONTQSA-N (1s,3z)-3-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCC(O)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C SNOXQOOPUCMFPS-ZLNGONTQSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004040 24-hydroxy-cholecalciferol Substances 0.000 abstract 1
- HIAJCGFYHIANNA-QIZZZRFXSA-N 3b-Hydroxy-5-cholenoic acid Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC(O)=O)C)[C@@]1(C)CC2 HIAJCGFYHIANNA-QIZZZRFXSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- -1 lithium aluminum hydride Chemical compound 0.000 abstract 1
- WQMNNHNWITXOAH-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].CC=[CH-] WQMNNHNWITXOAH-UHFFFAOYSA-M 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 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: The reduction reaction of a 24-oxo-Δ25-cholesterol is conducted in an inert organic solvent in the presence of a specific optically active compound to produce the titled compound in high yield, which is used as an intermediate of 24-hydroxycholecalciferol.
CONSTITUTION: A compound of formula I (R1 is H, protecting group; R2 is H, hydroxyl, protected hydroxyl) is reduced with lithium aluminum hydride in an inert solvent such as tetrahydrofuran in the presence of optically active 2,2'-dihydroxy- 1,1'-binaphthyl and a lower aliphatic alcohol such as methanol to produce 24(R) or 24(S)-hydroxycholesterol. The reaction temperature is -200W50°C. The starting material, the compound of formula I, is novel and obtained by reaction of 3β- tetrahydropyranyloxy-chol-5-ene-24-al derived from cholenic acid with propenylmagnesium bromide, followed by oxidation.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9051980A JPS5716899A (en) | 1980-07-04 | 1980-07-04 | Production of 24 (r) or 24 (s)-hydroxycholesterol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9051980A JPS5716899A (en) | 1980-07-04 | 1980-07-04 | Production of 24 (r) or 24 (s)-hydroxycholesterol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5716899A true JPS5716899A (en) | 1982-01-28 |
| JPS6314720B2 JPS6314720B2 (en) | 1988-04-01 |
Family
ID=14000691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9051980A Granted JPS5716899A (en) | 1980-07-04 | 1980-07-04 | Production of 24 (r) or 24 (s)-hydroxycholesterol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5716899A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58187382A (en) * | 1982-04-26 | 1983-11-01 | Matsushita Electric Ind Co Ltd | Printer |
| JPH0650305U (en) * | 1993-09-06 | 1994-07-08 | 北陸電気工業株式会社 | Variable resistor for high voltage |
-
1980
- 1980-07-04 JP JP9051980A patent/JPS5716899A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58187382A (en) * | 1982-04-26 | 1983-11-01 | Matsushita Electric Ind Co Ltd | Printer |
| JPH0261396B2 (en) * | 1982-04-26 | 1990-12-19 | Matsushita Electric Ind Co Ltd | |
| JPH0650305U (en) * | 1993-09-06 | 1994-07-08 | 北陸電気工業株式会社 | Variable resistor for high voltage |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6314720B2 (en) | 1988-04-01 |
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