CA1167461A - Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique - Google Patents

Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique

Info

Publication number: CA1167461A
Authority: CA; Canada
Prior art keywords: dimethyl; methyl; benzyloxy; hydroxy; octane
Prior art date: 1979-06-18
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

Application number

CA000419135A

Other languages

English (en)

Inventor

Michael P. Wachter

Zoltan G. Hajos

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ortho Pharmaceutical Corp

Original Assignee

Ortho Pharmaceutical Corp

Priority date (The priority date 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 date listed.)

1979-06-18

Filing date

1983-01-07

Publication date

1984-05-15

1979-06-18 Priority claimed from US06/049,760 external-priority patent/US4237055A/en

1983-01-07 Application filed by Ortho Pharmaceutical Corp filed Critical Ortho Pharmaceutical Corp

1983-01-07 Priority to CA000419135A priority Critical patent/CA1167461A/fr

1984-05-15 Application granted granted Critical

1984-05-15 Publication of CA1167461A publication Critical patent/CA1167461A/fr

Status Expired legal-status Critical Current

Links

230000015572 biosynthetic process Effects 0.000 title description 9
238000003786 synthesis reaction Methods 0.000 title description 8
239000000543 intermediate Substances 0.000 title description 5
-1 hydroxy, methoxy Chemical group 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
230000003301 hydrolyzing effect Effects 0.000 claims 2
239000007818 Grignard reagent Substances 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
150000004795 grignard reagents Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
239000012267 brine Substances 0.000 description 38
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
239000002904 solvent Substances 0.000 description 35
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 25
239000000243 solution Substances 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 23
101150041968 CDC13 gene Proteins 0.000 description 22
150000002576 ketones Chemical class 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
239000000284 extract Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
229960000443 hydrochloric acid Drugs 0.000 description 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
235000019439 ethyl acetate Nutrition 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000007832 Na2SO4 Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
150000002500 ions Chemical class 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
229910001868 water Inorganic materials 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
229940073584 methylene chloride Drugs 0.000 description 6
IEBBEWQHXJJMNB-UHFFFAOYSA-N oxepan-2-ol Chemical compound OC1CCCCCO1 IEBBEWQHXJJMNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
AWNHDBQTEISGRL-UHFFFAOYSA-N (8-chloro-2,6-dimethyloct-6-enoxy)methylbenzene Chemical compound ClCC=C(C)CCCC(C)COCC1=CC=CC=C1 AWNHDBQTEISGRL-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 3
230000002301 combined effect Effects 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
229940093858 ethyl acetoacetate Drugs 0.000 description 3
235000019256 formaldehyde Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
OMXFLKIYWVFEGA-UHFFFAOYSA-N (6,10-dimethyl-11-phenylmethoxyundeca-1,5-dien-2-yl)oxy-trimethylsilane Chemical compound C[Si](C)(C)OC(=C)CCC=C(C)CCCC(C)COCC1=CC=CC=C1 OMXFLKIYWVFEGA-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
VZUGAJIKBVMJFY-UHFFFAOYSA-N 2-methyl-2-(4-methylpent-4-enyl)-1,3-dioxolane Chemical compound CC(=C)CCCC1(C)OCCO1 VZUGAJIKBVMJFY-UHFFFAOYSA-N 0.000 description 2
KTOZOIWMZNVSDN-UHFFFAOYSA-N 2-methyl-5-(2-methyl-1,3-dioxolan-2-yl)pentan-1-ol Chemical compound OCC(C)CCCC1(C)OCCO1 KTOZOIWMZNVSDN-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
BDTKASCHWPOXLQ-UHFFFAOYSA-N 6-methyl-7-phenylmethoxyheptan-2-one Chemical compound CC(=O)CCCC(C)COCC1=CC=CC=C1 BDTKASCHWPOXLQ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
XRDHAXIOHKTIGF-JECBFZOVSA-N Zoapatanol Chemical compound CC(C)=CCC(=O)[C@H](C)CCC[C@]1(C)OC\C(=C\CO)CC[C@H]1O XRDHAXIOHKTIGF-JECBFZOVSA-N 0.000 description 2
XRDHAXIOHKTIGF-UHFFFAOYSA-N Zoapatanol Natural products CC(C)=CCC(=O)C(C)CCCC1(C)OCC(=CCO)CCC1O XRDHAXIOHKTIGF-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
150000003333 secondary alcohols Chemical class 0.000 description 2
150000003385 sodium Chemical class 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
DHEOFCCHPFFFMZ-UHFFFAOYSA-N (8-bromo-2,6-dimethyloct-6-enoxy)-tert-butyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(CCCC(C)=CCBr)C)C1=CC=CC=C1 DHEOFCCHPFFFMZ-UHFFFAOYSA-N 0.000 description 1
YHLSTYHLZMTWOB-UHFFFAOYSA-N (8-bromo-2,6-dimethyloct-6-enoxy)methylbenzene Chemical compound BrCC=C(C)CCCC(C)COCC1=CC=CC=C1 YHLSTYHLZMTWOB-UHFFFAOYSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
WYKMZXRYSTVIEX-UHFFFAOYSA-N 1-bromo-11-[tert-butyl(diphenyl)silyl]oxy-6,10-dimethylundec-5-en-2-one Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(CCCC(C)=CCCC(=O)CBr)C)C1=CC=CC=C1 WYKMZXRYSTVIEX-UHFFFAOYSA-N 0.000 description 1
LQMDUPCQYGCDHF-UHFFFAOYSA-N 2-(3,8-dioxabicyclo[3.2.1]octan-5-yl)acetic acid Chemical compound C1OCC2CCC1(CC(=O)O)O2 LQMDUPCQYGCDHF-UHFFFAOYSA-N 0.000 description 1
LVTXXWDEQRKQNA-UHFFFAOYSA-N 2-(bromomethyl)-5-(2-hydroxy-6-methyl-7-phenylmethoxyheptan-2-yl)oxolan-2-ol Chemical compound C=1C=CC=CC=1COCC(C)CCCC(C)(O)C1CCC(O)(CBr)O1 LVTXXWDEQRKQNA-UHFFFAOYSA-N 0.000 description 1
NBEXPGJVQUUVAT-UHFFFAOYSA-N 2-(bromomethyl)-5-[7-[tert-butyl(diphenyl)silyl]oxy-2-hydroxy-6-methylheptan-2-yl]oxolan-2-ol Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(C=1C=CC=CC=1)OCC(C)CCCC(C)(O)C1CCC(O)(CBr)O1 NBEXPGJVQUUVAT-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
WOPYURXQWMHYFG-UHFFFAOYSA-N 2-[2-(5-hydroxy-4,8-dimethylnon-7-enyl)-2-methyl-3,8-dioxabicyclo[3.2.1]octan-5-yl]acetic acid Chemical compound CC(C)=CCC(O)C(C)CCCC1(C)OCC2(CC(O)=O)CCC1O2 WOPYURXQWMHYFG-UHFFFAOYSA-N 0.000 description 1
HKNVWLNUJBGUTF-UHFFFAOYSA-N 2-[5-(bromomethyl)-5-methoxyoxolan-2-yl]-7-[tert-butyl(diphenyl)silyl]oxy-6-methylheptan-2-ol Chemical compound O1C(OC)(CBr)CCC1C(C)(O)CCCC(C)CO[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 HKNVWLNUJBGUTF-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
BRSOQCABRZMHEV-UHFFFAOYSA-N 3,7-dimethyl-8-phenylmethoxyoct-1-en-3-ol Chemical compound C=CC(C)(O)CCCC(C)COCC1=CC=CC=C1 BRSOQCABRZMHEV-UHFFFAOYSA-N 0.000 description 1
IUDWWFNDSJRYRV-UHFFFAOYSA-N 3,7-dimethyloct-1-en-3-ol Chemical compound CC(C)CCCC(C)(O)C=C IUDWWFNDSJRYRV-UHFFFAOYSA-N 0.000 description 1
YWJYHOMUEWSGQJ-UHFFFAOYSA-N 3,8-dioxabicyclo[3.2.1]octane Chemical compound C1OCC2CCC1O2 YWJYHOMUEWSGQJ-UHFFFAOYSA-N 0.000 description 1
RTUGXWDGYGFKLU-UHFFFAOYSA-N 4-[3-methyl-3-(4-methylpentyl)oxiran-2-yl]butan-2-one Chemical compound CC1(C(CCC(C)=O)O1)CCCC(C)C RTUGXWDGYGFKLU-UHFFFAOYSA-N 0.000 description 1
KDOFXENMXVYCEJ-UHFFFAOYSA-N 5-(2-methyl-1,3-dioxolan-2-yl)pentan-2-one Chemical compound CC(=O)CCCC1(C)OCCO1 KDOFXENMXVYCEJ-UHFFFAOYSA-N 0.000 description 1
COFFUYZBRGBAQS-UHFFFAOYSA-N 6,10-dimethylundec-5-en-2-one Chemical compound CC(C)CCCC(C)=CCCC(C)=O COFFUYZBRGBAQS-UHFFFAOYSA-N 0.000 description 1
BTSPQYKZKWYOFZ-UHFFFAOYSA-N 8-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethyloct-1-en-3-ol Chemical compound C=1C=CC=CC=1[Si](C(C)(C)C)(OCC(CCCC(C)(O)C=C)C)C1=CC=CC=C1 BTSPQYKZKWYOFZ-UHFFFAOYSA-N 0.000 description 1
XRDHAXIOHKTIGF-UKHUEATNSA-N 9-[(2r,3s,6e)-3-hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2-yl]-2,6-dimethylnon-2-en-5-one Chemical compound CC(C)=CCC(=O)C(C)CCC[C@@]1(C)OC\C(=C\CO)CC[C@@H]1O XRDHAXIOHKTIGF-UKHUEATNSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
241000196224 Codium Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CQXCEINEIDRVDO-UHFFFAOYSA-M O.[OH-].[Na+].OC.C1COCCO1 Chemical compound O.[OH-].[Na+].OC.C1COCCO1 CQXCEINEIDRVDO-UHFFFAOYSA-M 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
241000212342 Sium Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
101100162169 Xenopus laevis adrm1-a gene Proteins 0.000 description 1
BDGHEIUOLPXCDY-UHFFFAOYSA-M [Br-].CC(=C)CC[Mg+] Chemical compound [Br-].CC(=C)CC[Mg+] BDGHEIUOLPXCDY-UHFFFAOYSA-M 0.000 description 1
DUVIDEDNZHKADB-UHFFFAOYSA-M [Li+].O.[OH-].OC.C1COCCO1 Chemical compound [Li+].O.[OH-].OC.C1COCCO1 DUVIDEDNZHKADB-UHFFFAOYSA-M 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
125000000746 allylic group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910000365 copper sulfate Inorganic materials 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
BNSYGCKJOAPBCM-UHFFFAOYSA-N heptan-2-ol Chemical compound [CH2]C(O)CCCCC BNSYGCKJOAPBCM-UHFFFAOYSA-N 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
229940091250 magnesium supplement Drugs 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
ONDXXAPHPJPFKQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphoryl]-n-methylmethanamine;oxolane Chemical compound C1CCOC1.CN(C)P(=O)(N(C)C)N(C)C ONDXXAPHPJPFKQ-UHFFFAOYSA-N 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000526 short-path distillation Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
YBBNUDDZOWRHOD-UHFFFAOYSA-N undec-6-enal Chemical compound CCCCC=CCCCCC=O YBBNUDDZOWRHOD-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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CA000419135A 1979-06-18 1983-01-07 Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique Expired CA1167461A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000419135A CA1167461A (fr)	1979-06-18	1983-01-07	Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/049,760 US4237055A (en)	1979-06-18	1979-06-18	Synthesis of 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo[3.2.1]octane-1-acetic acid
US049,760		1979-06-18
CA000353115A CA1149403A (fr)	1979-06-18	1980-05-30	Synthese d'acide 1rs,4sr,5rs-4-(4,8-dimethyl-5- hydroxy-7-nonen-1-yl)-4-methyl-3,8- dioxabicyclo ¬3.2.1\| octane-1-acetique
CA000419135A CA1167461A (fr)	1979-06-18	1983-01-07	Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique

Publications (1)

Publication Number	Publication Date
CA1167461A true CA1167461A (fr)	1984-05-15

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000419135A Expired CA1167461A (fr)	1979-06-18	1983-01-07	Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique

Country Status (1)

Country	Link
CA (1)	CA1167461A (fr)

1983
- 1983-01-07 CA CA000419135A patent/CA1167461A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-05-15	MKEX	Expiry

Publication	Publication Date	Title
Fleming et al.	1984	Stereospecific syntheses and reactions of allyl-and allenyl-silanes
EP0045118B1 (fr)	1984-04-04	Intermédiaires pour la synthèse de bicyclo (2,2,1) heptanes et bicyclo (2,2,1) hept-2Z-ènes
Ireland et al.	1984	Total synthesis of (.+-.)-aphidicolin and (.+-.)-. beta.-chamigrene
Kinney et al.	1983	Regiocontrolled synthesis of mono-, di-, and trisubstituted cyclohexenones by cycloaddition of vinyl sulfones to 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadienes. Conversion of alkenes into effective dienophilic reagents
CA1149403A (fr)	1983-07-05	Synthese d'acide 1rs,4sr,5rs-4-(4,8-dimethyl-5- hydroxy-7-nonen-1-yl)-4-methyl-3,8- dioxabicyclo ¬3.2.1\| octane-1-acetique
US4983766A (en)	1991-01-08	Optically active B hydroxy acids
EP0183132B1 (fr)	1989-10-18	Procédé de préparation des inhibiteurs de HMG-CoA réductase et intermédiaires utilisés
KR101451979B1 (ko)	2014-10-21	테트라하이드로피란-3-온으로부터 테트라하이드로피란의제조 방법
CA1167461A (fr)	1984-05-15	Produits interediaires pour la synthese d'acide 1rs, 4rs, 5rs-4-(4,8-dimethyl-5-hydroxy- 7-nonen-1-yl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetique
Wada et al.	1989	New synthesis of 2-oxo-3-alkenylphosphonates and hetero Diels-Alder reactions with vinyl ethers leading to 5-substituted 2-phosphinyl-2-cyclohexen-1-ones.
US4163758A (en)	1979-08-07	2-Nitroethylcyclopentane compounds and process for preparing the same
Yadav et al.	2008	Stereoconvergent synthesis of C1–C17 and C18–C25 fragments of bafilomycin A1
CA2000179C (fr)	2000-05-02	Derives de l'acide cyclopenteneheptenoique et methode pour sa preparation
Davidson et al.	1990	Intramolecular Diels-Alder approach to cadinane and amorphane sesquiterpenes
US4009196A (en)	1977-02-22	2-Acyl-3-substituted cyclopentan-1-ones and process for their preparation
CA1170266A (fr)	1984-07-03	Synthese complete d'acide lrs, 4sr, 5rs- 4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8- dioxabicylo¬octane-1-acetique, et composes apparentes
Pearson et al.	1982	Organoiron complexes in organic synthesis. Part 23. New strategies for steroid and aphidicolane synthesis
Hajos et al.	1984	Total synthesis of (1RS, 4SR, 5RS)-4-(5-hydroxy-4, 8-dimethyl-7-nonen-1-yl)-4-methyl-3, 8-dioxabicyclo [3.2. 1] octane-1-acetic acid from geraniol
CA1173051A (fr)	1984-08-21	Synthese totale d'acide 1rs,4sr,srs-4- (4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8- dioxabicyclo¬3.2.1\| octane-1-acetique
Baker et al.	1985	Stereoselective synthesis of (±)-ancistrofuran and its stereoisomers
Inouye et al.	1987	Preparation of bicyclo [3.3. 1] nonane-2, 4-dione derivatives.
Lan et al.	1999	The first total synthesis of preverecynarmin
US4177197A (en)	1979-12-04	Cyclization substrates and 7α-substituted 19-norsteroid derivatives
EP0012622B1 (fr)	1982-12-15	1-Tosyloxy-2,2-ethylène dioxy-6,10-diméthyl-undécanes et undécènes,procédé pour la préparation de 2S,3R-3-benzyloxy-6,6-éthylènedioxy-2-méthyl-2-(5'-hydroxy-4-méthylpentyl)-oxépane et utilisation du dernier pour la préparation de dérives de l'oxepan-3-o
Houwen-Claassen et al.	1989	Selective bis-hydride reduction of tosylmethyl-substituted tricyclic enones by lithium aluminium hydride synthesis of α-methylene cyclopentenoids