JPS6338019B2 - - Google Patents

Info

Publication number: JPS6338019B2
Authority: JP; Japan
Prior art keywords: reaction; solvent; polyprenyl; general formula; formula
Prior art date: 1982-04-06
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

JP57057863A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58174351A (ja

Inventor

Tetsuo Takigawa

Koichi Kinuhata

Masafumi Okada

Masao Mizuno

Takuji Nishida

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.)

Kuraray Co Ltd

Original Assignee

Kuraray Co Ltd

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.)

1982-04-06

Filing date

1982-04-06

Publication date

1988-07-28

1982-04-06 Application filed by Kuraray Co Ltd filed Critical Kuraray Co Ltd

1982-04-06 Priority to JP57057863A priority Critical patent/JPS58174351A/ja

1983-02-17 Priority to US06/467,253 priority patent/US4564477A/en

1983-02-18 Priority to EP83101562A priority patent/EP0087136B1/en

1983-02-18 Priority to DE8383101562T priority patent/DE3360448D1/de

1983-10-13 Publication of JPS58174351A publication Critical patent/JPS58174351A/ja

1988-07-28 Publication of JPS6338019B2 publication Critical patent/JPS6338019B2/ja

Status Granted legal-status Critical Current

Links

RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 68
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 45
239000002904 solvent Substances 0.000 description 40
125000001185 polyprenyl group Polymers 0.000 description 37
239000002253 acid Substances 0.000 description 34
229920001550 polyprenyl Polymers 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
238000004458 analytical method Methods 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
150000002148 esters Chemical class 0.000 description 24
239000007788 liquid Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
150000002031 dolichols Chemical class 0.000 description 19
239000000203 mixture Substances 0.000 description 19
239000000243 solution Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
229920001731 Polyprenol Polymers 0.000 description 14
229930186185 Polyprenol Natural products 0.000 description 14
150000004820 halides Chemical class 0.000 description 13
150000003096 polyprenols Chemical class 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 12
BDMCAOBQLHJGBE-UHFFFAOYSA-N C60-polyprenol Natural products CC(=CCCC(=CCCC(=CCCC(=CCCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CO)C)C)C)C)C)C)C)C)C)C)C)C BDMCAOBQLHJGBE-UHFFFAOYSA-N 0.000 description 11
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 11
238000003756 stirring Methods 0.000 description 11
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
-1 containing 14 Chemical class 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
239000000047 product Substances 0.000 description 10
150000002825 nitriles Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
239000002585 base Substances 0.000 description 7
150000007514 bases Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
239000003463 adsorbent Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000010410 layer Substances 0.000 description 4
210000004185 liver Anatomy 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
235000009109 Betula pendula Nutrition 0.000 description 2
241000219430 Betula pendula Species 0.000 description 2
241000218646 Cedrus deodara Species 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000282887 Suidae Species 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000011344 liquid material Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
235000005251 Dioscorea japonica Nutrition 0.000 description 1
240000008955 Dioscorea japonica Species 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
239000012448 Lithium borohydride Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
240000007320 Pinus strobus Species 0.000 description 1
235000008578 Pinus strobus Nutrition 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000700159 Rattus Species 0.000 description 1
240000004111 Scaphochlamys sylvestris Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000992309 Strobus Species 0.000 description 1
YZWMUTWKHHJGHC-UHFFFAOYSA-N acetamide;acetic acid Chemical compound CC(N)=O.CC(O)=O YZWMUTWKHHJGHC-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000032683 aging Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
ALSPKRWQCLSJLV-UHFFFAOYSA-N azanium;acetic acid;acetate Chemical compound [NH4+].CC(O)=O.CC([O-])=O ALSPKRWQCLSJLV-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
244000309466 calf Species 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
238000004891 communication Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000039 congener Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000002397 field ionisation mass spectrometry Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Medicines Containing Plant Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP57057863A 1982-02-19 1982-04-06 ジヒドロポリプレニルニトリル Granted JPS58174351A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP57057863A JPS58174351A (ja)	1982-04-06	1982-04-06	ジヒドロポリプレニルニトリル
US06/467,253 US4564477A (en)	1982-02-19	1983-02-17	Polyprenyl compounds and method of producing the same
EP83101562A EP0087136B1 (en)	1982-02-19	1983-02-18	Novel polyprenyl compounds, method of producing the same and their use in dolichol production
DE8383101562T DE3360448D1 (en)	1982-02-19	1983-02-18	Novel polyprenyl compounds, method of producing the same and their use in dolichol production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57057863A JPS58174351A (ja)	1982-04-06	1982-04-06	ジヒドロポリプレニルニトリル

Publications (2)

Publication Number	Publication Date
JPS58174351A JPS58174351A (ja)	1983-10-13
JPS6338019B2 true JPS6338019B2 (pt)	1988-07-28

Family

ID=13067829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57057863A Granted JPS58174351A (ja)	1982-02-19	1982-04-06	ジヒドロポリプレニルニトリル

Country Status (1)

Country	Link
JP (1)	JPS58174351A (pt)

1982
- 1982-04-06 JP JP57057863A patent/JPS58174351A/ja active Granted

Also Published As

Publication number	Publication date
JPS58174351A (ja)	1983-10-13

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