SU497762A3 - Способ получени оптически активных соединений простагландинового р да - Google Patents
Способ получени оптически активных соединений простагландинового р даInfo
- Publication number
- SU497762A3 SU497762A3 SU1839641A SU1839641A SU497762A3 SU 497762 A3 SU497762 A3 SU 497762A3 SU 1839641 A SU1839641 A SU 1839641A SU 1839641 A SU1839641 A SU 1839641A SU 497762 A3 SU497762 A3 SU 497762A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- optically active
- active compounds
- trimethylsilyl
- ester
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title description 22
- 238000000034 method Methods 0.000 title description 8
- 150000003180 prostaglandins Chemical class 0.000 title description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000006884 silylation reaction Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- 239000012027 Collins reagent Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00190667A US3822303A (en) | 1971-10-19 | 1971-10-19 | Trimethyl silyl esters of prostaglandin e acids and esters and process therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU497762A3 true SU497762A3 (ru) | 1975-12-30 |
Family
ID=22702287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1839641A SU497762A3 (ru) | 1971-10-19 | 1972-10-16 | Способ получени оптически активных соединений простагландинового р да |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3822303A (enExample) |
| JP (1) | JPS5225B2 (enExample) |
| AR (1) | AR196311A1 (enExample) |
| CA (1) | CA973176A (enExample) |
| CH (1) | CH592055A5 (enExample) |
| DK (1) | DK145462C (enExample) |
| ES (1) | ES407629A1 (enExample) |
| FI (1) | FI55994C (enExample) |
| HU (1) | HU166952B (enExample) |
| NL (1) | NL153183B (enExample) |
| NO (2) | NO138024C (enExample) |
| PL (1) | PL94475B1 (enExample) |
| SE (2) | SE389669B (enExample) |
| SU (1) | SU497762A3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4737590A (en) * | 1973-04-27 | 1988-04-12 | American Cyanamid Company | Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones |
| US4324905A (en) * | 1974-08-14 | 1982-04-13 | The Upjohn Company | Phenacyl-type esters of PGF2α and its 15-methyl analogs |
| JPS56176887U (enExample) * | 1980-05-31 | 1981-12-26 | ||
| KR20010041632A (ko) * | 1998-03-06 | 2001-05-25 | 아스트라제네카 악티에볼라그 | 신규 방법 |
-
1971
- 1971-10-19 US US00190667A patent/US3822303A/en not_active Expired - Lifetime
-
1972
- 1972-09-07 AR AR243957A patent/AR196311A1/es active
- 1972-09-22 CH CH1384472A patent/CH592055A5/xx not_active IP Right Cessation
- 1972-09-25 CA CA152,446A patent/CA973176A/en not_active Expired
- 1972-10-06 FI FI2769/72A patent/FI55994C/fi active
- 1972-10-11 JP JP47101207A patent/JPS5225B2/ja not_active Expired
- 1972-10-12 DK DK504072A patent/DK145462C/da not_active IP Right Cessation
- 1972-10-14 ES ES407629A patent/ES407629A1/es not_active Expired
- 1972-10-16 SU SU1839641A patent/SU497762A3/ru active
- 1972-10-17 PL PL1972158317A patent/PL94475B1/pl unknown
- 1972-10-18 NO NO3734/72A patent/NO138024C/no unknown
- 1972-10-18 SE SE7213425A patent/SE389669B/xx unknown
- 1972-10-19 NL NL727214142A patent/NL153183B/xx not_active IP Right Cessation
- 1972-10-19 HU HUUO82A patent/HU166952B/hu unknown
-
1973
- 1973-12-03 NO NO4600/73A patent/NO138529C/no unknown
-
1975
- 1975-07-15 SE SE7508078A patent/SE7508078L/ not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK145462B (da) | 1982-11-22 |
| SE7508078L (sv) | 1975-07-15 |
| FI55994C (fi) | 1979-11-12 |
| JPS4852745A (enExample) | 1973-07-24 |
| PL94475B1 (pl) | 1977-08-31 |
| DK145462C (da) | 1983-04-25 |
| NO138529B (no) | 1978-06-12 |
| SE389669B (sv) | 1976-11-15 |
| NO138024B (no) | 1978-03-06 |
| NL7214142A (enExample) | 1973-04-25 |
| US3822303A (en) | 1974-07-02 |
| ES407629A1 (es) | 1976-10-16 |
| NO138024C (no) | 1978-06-14 |
| JPS5225B2 (enExample) | 1977-01-05 |
| AR196311A1 (es) | 1973-12-18 |
| NO138529C (no) | 1978-09-20 |
| CA973176A (en) | 1975-08-19 |
| CH592055A5 (enExample) | 1977-10-14 |
| FI55994B (fi) | 1979-07-31 |
| HU166952B (enExample) | 1975-06-28 |
| NL153183B (nl) | 1977-05-16 |
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