DE2911618C2 - - Google Patents
Info
- Publication number
- DE2911618C2 DE2911618C2 DE2911618A DE2911618A DE2911618C2 DE 2911618 C2 DE2911618 C2 DE 2911618C2 DE 2911618 A DE2911618 A DE 2911618A DE 2911618 A DE2911618 A DE 2911618A DE 2911618 C2 DE2911618 C2 DE 2911618C2
- Authority
- DE
- Germany
- Prior art keywords
- gibberellin
- aldehyde
- epigibberellin
- mmol
- aldehydes
- 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
- 239000003448 gibberellin Substances 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 43
- 229930191978 Gibberellin Natural products 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 33
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 claims description 27
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 17
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 229910052722 tritium Inorganic materials 0.000 claims description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 14
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003172 aldehyde group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- JLJLRLWOEMWYQK-OBDJNFEBSA-N gibberellin A1 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)CC2 JLJLRLWOEMWYQK-OBDJNFEBSA-N 0.000 claims description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052786 argon Inorganic materials 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 239000011651 chromium Substances 0.000 claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
- JLJLRLWOEMWYQK-UHFFFAOYSA-N Pseudogibberellin-A1 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(OC3=O)C1C3(C)C(O)CC2 JLJLRLWOEMWYQK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006345 epimerization reaction Methods 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000012300 argon atmosphere Substances 0.000 claims description 5
- -1 chromium peroxide Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 5
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- ZWPVWTIRZYDPKW-UHFFFAOYSA-N chromium(VI) oxide peroxide Inorganic materials [O-2].[O-][Cr]([O-])(=O)=O ZWPVWTIRZYDPKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005837 enolization reaction Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- ANYSGBYRTLOUPO-UHFFFAOYSA-N lithium tetramethylpiperidide Chemical compound [Li]N1C(C)(C)CCCC1(C)C ANYSGBYRTLOUPO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 88
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000007832 Na2SO4 Substances 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
- 235000011152 sodium sulphate Nutrition 0.000 description 25
- 238000003756 stirring Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- 239000012362 glacial acetic acid Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 238000010828 elution Methods 0.000 description 16
- 150000001299 aldehydes Chemical class 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000005051 trimethylchlorosilane Substances 0.000 description 4
- ZOWHLBOPCIHIHW-UHFFFAOYSA-N Gibberellin A5 Natural products C12CCC(C3)(O)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OC21CC=C3 ZOWHLBOPCIHIHW-UHFFFAOYSA-N 0.000 description 3
- MHVYWTXXZIFXDT-UHFFFAOYSA-N Gibberellin A9 Natural products C12CCC(C3)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OC21CCC3 MHVYWTXXZIFXDT-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229940082150 encore Drugs 0.000 description 3
- SEEGHKWOBVVBTQ-NFMPGMCNSA-N gibberellin A7 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 SEEGHKWOBVVBTQ-NFMPGMCNSA-N 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium dioxide Chemical compound O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- RSQSQJNRHICNNH-NFMPGMCNSA-N gibberellin A4 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)CC2 RSQSQJNRHICNNH-NFMPGMCNSA-N 0.000 description 2
- ZOWHLBOPCIHIHW-KQBHUUJHSA-N gibberellin A5 Chemical compound C([C@H]12)C[C@@](C3)(O)C(=C)C[C@@]13[C@@H](C(O)=O)[C@@H]1[C@]3(C)C(=O)O[C@@]12CC=C3 ZOWHLBOPCIHIHW-KQBHUUJHSA-N 0.000 description 2
- MHVYWTXXZIFXDT-YGNOGLJPSA-N gibberellin A9 Chemical compound C([C@H]12)C[C@H](C3)C(=C)C[C@@]13[C@@H](C(O)=O)[C@@H]1[C@]3(C)C(=O)O[C@@]12CCC3 MHVYWTXXZIFXDT-YGNOGLJPSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- UJFQJDAESQJXTG-UHFFFAOYSA-N Gibberellin A12 Natural products OC(=O)C1C2(CC3=C)CC3CCC2C2(C)C1C(C)(C(O)=O)CCC2 UJFQJDAESQJXTG-UHFFFAOYSA-N 0.000 description 1
- ZCTUNYRXJKLWPY-UHFFFAOYSA-N Gibberellin A12 7-aldehyde Natural products O=CC1C2(CC3=C)CC3CCC2C2(C)C1C(C)(C(O)=O)CCC2 ZCTUNYRXJKLWPY-UHFFFAOYSA-N 0.000 description 1
- MXCOJKLBLFWFNI-VBFYFJBNSA-N Gibberellin A15 Natural products O=C(O)[C@H]1[C@@H]2[C@@]3(C)C(=O)OC[C@]2([C@H]2[C@@]41CC(=C)[C@H](C4)CC2)CCC3 MXCOJKLBLFWFNI-VBFYFJBNSA-N 0.000 description 1
- BKBYHSYZKIAJDA-UHFFFAOYSA-N Gibberellin A29 Natural products C12CCC(C3)(O)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OC21CC(O)C3 BKBYHSYZKIAJDA-UHFFFAOYSA-N 0.000 description 1
- NYLKJADFYRJQOI-DMQYUYNFSA-N Gibberellin A35 Natural products C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)[C@H](O)[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)CC2 NYLKJADFYRJQOI-DMQYUYNFSA-N 0.000 description 1
- RSQSQJNRHICNNH-UHFFFAOYSA-N Gibberellin A4 Natural products OC(=O)C1C2(CC3=C)CC3CCC2C2(OC3=O)C1C3(C)C(O)CC2 RSQSQJNRHICNNH-UHFFFAOYSA-N 0.000 description 1
- KSBJAONOPKRVRR-UHFFFAOYSA-N Gibberellin A44 Natural products C12CCC(C3)(O)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OCC21CCC3 KSBJAONOPKRVRR-UHFFFAOYSA-N 0.000 description 1
- FKMJLJSSQHSAEF-WQODXWHISA-N Gibberellin A50 Natural products O=C(O)[C@H]1[C@@H]2[C@@]3(C)[C@@H](O)[C@@H](O)C[C@@]2(OC3=O)[C@@H]2[C@@H](O)C[C@H]3C(=C)C[C@@]12C3 FKMJLJSSQHSAEF-WQODXWHISA-N 0.000 description 1
- HHDWSDSMWJQURA-UHFFFAOYSA-N Gibberellin A51 Natural products C12CCC(C3)C(=C)CC23C(C(O)=O)C2C3(C)C(=O)OC21CC(O)C3 HHDWSDSMWJQURA-UHFFFAOYSA-N 0.000 description 1
- JKQCGVABHHQYKQ-YZVDRFENSA-N Gibberellin A61 Natural products O=C(O)[C@H]1[C@@H]2[C@]3(C)C(=O)O[C@]2([C@H](O)CC3)[C@H]2[C@]31CC(=C)[C@@H](C3)CC2 JKQCGVABHHQYKQ-YZVDRFENSA-N 0.000 description 1
- WZRRJZYYGOOHRC-UQJCXHNCSA-N Gibberellin A8 Natural products C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@@]2(OC3=O)[C@H]1[C@@]3(C)[C@@H](O)[C@@H](O)C2 WZRRJZYYGOOHRC-UQJCXHNCSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 1
- 241000773293 Rappaport Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IXORZMNAPKEEDV-OHSBXDGMSA-N berelex Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)C1[C@@]3(C)C(=O)O2 IXORZMNAPKEEDV-OHSBXDGMSA-N 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- WZRRJZYYGOOHRC-UHFFFAOYSA-N gibberellic acid 8 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(OC3=O)C1C3(C)C(O)C(O)C2 WZRRJZYYGOOHRC-UHFFFAOYSA-N 0.000 description 1
- UJFQJDAESQJXTG-UFUZVNNQSA-N gibberellin A12 Chemical compound C([C@@H]1C[C@]2(CC1=C)[C@H]1C(O)=O)C[C@H]2[C@@]2(C)[C@H]1[C@](C)(C(O)=O)CCC2 UJFQJDAESQJXTG-UFUZVNNQSA-N 0.000 description 1
- SEEGHKWOBVVBTQ-UHFFFAOYSA-N gibberellin GA7 Natural products OC(=O)C1C2(CC3=C)CC3CCC2C2(C=CC3O)C1C3(C)C(=O)O2 SEEGHKWOBVVBTQ-UHFFFAOYSA-N 0.000 description 1
- GFEIVLLXVCBXOQ-UHFFFAOYSA-N gibberelline Natural products CC12CCCC3(C(O)OC1=O)C4CCC5(O)CC4(CC5=C)C(C23)C(=O)O GFEIVLLXVCBXOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD20477178A DD135726B1 (de) | 1978-04-13 | 1978-04-13 | Verfahren zur herstellung von c tief 19-gibberellinaldehyden |
| DD20476978A DD135725A1 (de) | 1978-04-13 | 1978-04-13 | Verfahren zur herstellung von gibberellin-verbindungen |
| DD20775878A DD138663B1 (de) | 1978-09-12 | 1978-09-12 | Verfahren zur epimerisierung von gibberellin-7-aldehyden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2911618A1 DE2911618A1 (de) | 1979-10-25 |
| DE2911618C2 true DE2911618C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-29 |
Family
ID=27179826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2911618A Granted DE2911618A1 (de) | 1978-04-13 | 1979-03-24 | Markierte gibberelline und verfahren zu ihrer herstellung |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039235A1 (de) * | 1980-10-17 | 1982-05-19 | Licentia Patent-Verwaltungs-Gmbh, 6000 Frankfurt | "druckempfindlicher, faseroptischer sensor" |
| US4426534A (en) | 1981-09-22 | 1984-01-17 | Thiokol Corporation | Method for producing aldehydes and ketones using 2,2'-bipyridinium chlorochromate as oxidizing agent |
| US4399281A (en) * | 1981-09-22 | 1983-08-16 | Thiokol Corporation | 2,2'-Bipyridinium chlorochromate oxidant |
| DK0588964T3 (da) * | 1991-06-14 | 1999-05-10 | Abbott Lab | Fremgangsmåde til adskillelse af gibberellinblandinger |
-
1979
- 1979-03-24 DE DE2911618A patent/DE2911618A1/de active Granted
- 1979-03-28 US US06/024,781 patent/US4282154A/en not_active Expired - Lifetime
- 1979-04-10 GB GB7912596A patent/GB2022576B/en not_active Expired
- 1979-04-11 HU HU79WI299A patent/HU184706B/hu unknown
- 1979-04-12 NL NL7902888A patent/NL7902888A/xx not_active Application Discontinuation
- 1979-04-13 FR FR7909539A patent/FR2438019A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2911618A1 (de) | 1979-10-25 |
| HU184706B (en) | 1984-10-29 |
| FR2438019B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-02-19 |
| US4282154A (en) | 1981-08-04 |
| NL7902888A (nl) | 1979-10-16 |
| GB2022576B (en) | 1983-03-30 |
| GB2022576A (en) | 1979-12-19 |
| FR2438019A1 (fr) | 1980-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8330 | Complete renunciation |