NO126322B - - Google Patents
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- Publication number
- NO126322B NO126322B NO01327/70A NO132770A NO126322B NO 126322 B NO126322 B NO 126322B NO 01327/70 A NO01327/70 A NO 01327/70A NO 132770 A NO132770 A NO 132770A NO 126322 B NO126322 B NO 126322B
- Authority
- NO
- Norway
- Prior art keywords
- mmol
- absolute
- dichloroethane
- dissolved
- theoretical
- Prior art date
Links
- 235000000346 sugar Nutrition 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000002718 pyrimidine nucleoside Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 20
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- 235000011150 stannous chloride Nutrition 0.000 description 20
- 239000001119 stannous chloride Substances 0.000 description 20
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002777 nucleoside Substances 0.000 description 9
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 150000003833 nucleoside derivatives Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- -1 trialkylsilyl halides Chemical class 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002168 ethanoic acid esters Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 150000002730 mercury Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- SAXGTQUYGSZANW-UPRLRBBYSA-N (2R,3R,4S)-3,4-dibenzoyl-2,3,4-trihydroxy-2-(hydroxymethyl)-1-phenylheptane-1,5,6-trione Chemical compound C(C)(=O)C(=O)[C@](O)([C@](O)([C@](O)(CO)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O SAXGTQUYGSZANW-UPRLRBBYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 239000012043 crude product Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical compound IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000003835 nucleoside group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DFPLOTUUYKPTGK-CSODTCANSA-N (2R,3R)-5-chloro-2-[hydroxy-(2-methylphenyl)methyl]-3-(2-methylphenyl)oxolan-3-ol Chemical compound C1(=C(C=CC=C1)[C@@]1(CC(O[C@@H]1C(O)C1=C(C=CC=C1)C)Cl)O)C DFPLOTUUYKPTGK-CSODTCANSA-N 0.000 description 1
- JKBRCYHNTCMICZ-ZQCUGPNOSA-N (3R,4R,5S)-4,5-dibenzoyl-2,3,4,5-tetrahydroxy-1-phenyloctane-1,6,7-trione Chemical compound C(C)(=O)C(=O)[C@](O)([C@](O)([C@H](O)C(O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O JKBRCYHNTCMICZ-ZQCUGPNOSA-N 0.000 description 1
- HHMSVTJEZKSKMU-IDKCCGAKSA-N 1-[(3S,4R,5R)-3,4-dibenzyl-2,3,4-trihydroxy-5-(1-hydroxy-2-phenylethyl)oxolan-2-yl]ethanone Chemical compound C(C)(=O)C1(O)[C@@](O)([C@](O)([C@H](O1)C(O)CC1=CC=CC=C1)CC1=CC=CC=C1)CC1=CC=CC=C1 HHMSVTJEZKSKMU-IDKCCGAKSA-N 0.000 description 1
- MZJSYLUUDHWYRK-JRVZRWKPSA-N 1-[(3S,4S,5R)-3,4,5-tribenzoyl-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]ethanone Chemical compound C(C)(=O)C1(O)[C@](O)([C@](O)([C@](O1)(CO)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O MZJSYLUUDHWYRK-JRVZRWKPSA-N 0.000 description 1
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- GMXHQGHCBUHALX-UHFFFAOYSA-N 5-iodo-4,6-dimethoxypyrimidine Chemical compound IC=1C(=NC=NC1OC)OC GMXHQGHCBUHALX-UHFFFAOYSA-N 0.000 description 1
- TUARVSWVPPVUGS-UHFFFAOYSA-N 5-nitrouracil Chemical compound [O-][N+](=O)C1=CNC(=O)NC1=O TUARVSWVPPVUGS-UHFFFAOYSA-N 0.000 description 1
- XZWMZFQOHTWGQE-UHFFFAOYSA-N 6-azathymine Chemical compound CC1=NNC(=O)NC1=O XZWMZFQOHTWGQE-UHFFFAOYSA-N 0.000 description 1
- NKOPQOSBROLOFP-UHFFFAOYSA-N 6-methyl-3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound CC1=NNC(=S)NC1=O NKOPQOSBROLOFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101100489867 Mus musculus Got2 gene Proteins 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- MPYUTOYNCCRZAC-VNSJUHMKSA-N [(2r,3r,4r,5r)-3,4-dibenzoyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound O([C@H]1[C@@H](O[C@@H]([C@H]1OC(=O)C=1C=CC=CC=1)COC(=O)C=1C=CC=CC=1)N1C(NC(=O)C=C1)=O)C(=O)C1=CC=CC=C1 MPYUTOYNCCRZAC-VNSJUHMKSA-N 0.000 description 1
- QHXONHVHMASILU-IYUNARRTSA-N [(2r,3r,4r,5r)-3,4-dibenzoyloxy-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound O=C1NC(=O)C(CC)=CN1[C@H]1[C@H](OC(=O)C=2C=CC=CC=2)[C@H](OC(=O)C=2C=CC=CC=2)[C@@H](COC(=O)C=2C=CC=CC=2)O1 QHXONHVHMASILU-IYUNARRTSA-N 0.000 description 1
- UAOKXEHOENRFMP-ZJIFWQFVSA-N [(2r,3r,4s,5r)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C=O UAOKXEHOENRFMP-ZJIFWQFVSA-N 0.000 description 1
- CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002682 anti-psoriatic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- QQOBRRFOVWGIMD-OJAKKHQRSA-N azaribine Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=N1 QQOBRRFOVWGIMD-OJAKKHQRSA-N 0.000 description 1
- 229950010054 azaribine Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical group [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/12—Triazine radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691919307 DE1919307C (de) | 1969-04-11 | Verfahren zur Herstellung von Nucleo siden | |
| DE19691943428 DE1943428C3 (de) | 1969-08-23 | 1969-08-23 | Verfahren zur Herstellung von Pyrimidin- und 6-Azauracilnueleosiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126322B true NO126322B (fr) | 1973-01-22 |
Family
ID=25757275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01327/70A NO126322B (fr) | 1969-04-11 | 1970-04-10 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3748320A (fr) |
| JP (1) | JPS52955B1 (fr) |
| AT (1) | AT315384B (fr) |
| BE (1) | BE748799A (fr) |
| CA (1) | CA931948A (fr) |
| CH (1) | CH541566A (fr) |
| DK (1) | DK126198B (fr) |
| ES (1) | ES378367A1 (fr) |
| FI (1) | FI54314C (fr) |
| FR (1) | FR2043174A5 (fr) |
| GB (1) | GB1313411A (fr) |
| IE (1) | IE33786B1 (fr) |
| IL (1) | IL34301A (fr) |
| NL (1) | NL166266B (fr) |
| NO (1) | NO126322B (fr) |
| PL (1) | PL93943B1 (fr) |
| SE (1) | SE363830B (fr) |
| SU (1) | SU452961A3 (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2066931A2 (en) * | 1970-10-30 | 1971-08-13 | Schering Ag | 2-thio -6-aza-uridine derivs |
| JPS4924977A (fr) * | 1972-06-30 | 1974-03-05 | ||
| US3868361A (en) * | 1973-03-12 | 1975-02-25 | Richard L Tolman | s-Triazolo{8 2,3-A{9 {0 pryimidine nucleosides |
| JPS5152183A (ja) * | 1974-10-28 | 1976-05-08 | Mitsui Seiyaku Kogyo Kk | Nukureoshidoruinoseizoho |
| JPS5195082A (en) * | 1975-02-14 | 1976-08-20 | 55 furuoroshichijinno seizoho | |
| DE2508312A1 (de) * | 1975-02-24 | 1976-09-02 | Schering Ag | Neues verfahren zur herstellung von nucleosiden |
| JPS51100087A (en) * | 1975-02-26 | 1976-09-03 | Mitsui Seiyaku Kogyo Kk | 11 * beeta dd arabinofuranoshiru * 55 furuoroshitoshinno seizoho |
| DE2514275A1 (de) * | 1975-03-27 | 1976-10-14 | Schering Ag | Verfahren zur herstellung von n- (polysaccharidyl)-stickstoffheterocyclen, insbesondere von pyrimidin- oder purinbasen |
| GB1531469A (en) * | 1975-12-18 | 1978-11-08 | Farmaceutici Italia | Daunosamine nucleosides |
| US4171431A (en) * | 1976-08-19 | 1979-10-16 | The Upjohn Company | Nucleosides and process |
| DE2721466A1 (de) * | 1977-05-12 | 1978-11-16 | Robugen Gmbh | Verfahren zur herstellung von 2'-desoxyribofuranosylnucleosiden |
| DE2757365A1 (de) * | 1977-12-20 | 1979-06-21 | Schering Ag | Neues verfahren zur herstellung von nucleosiden |
| GB1601020A (en) | 1978-04-24 | 1981-10-21 | Stichting Grega Vzw | 2'-deoxy-5 (2-halogenovinyl)-uridines |
| US4423212A (en) * | 1980-12-18 | 1983-12-27 | The Upjohn Company | Nucleosides and process |
| US4929723A (en) * | 1987-07-21 | 1990-05-29 | Ethyl Corporation | Process for preparing 2-deoxynucleosides |
| CA1301166C (fr) * | 1987-07-21 | 1992-05-19 | John Nicholas Freskos | Procede pour la preparation de 2-desoxynucleosides |
| US4914233A (en) * | 1988-03-01 | 1990-04-03 | Ethyl Corporation | Synthesis of beta-thymidine |
| JPH0217199A (ja) * | 1988-07-05 | 1990-01-22 | Japan Tobacco Inc | ２’−デオキシ−β−アデノシンの製造方法 |
| US5134066A (en) * | 1989-08-29 | 1992-07-28 | Monsanto Company | Improved probes using nucleosides containing 3-dezauracil analogs |
| CA2091732C (fr) * | 1992-07-08 | 1998-07-21 | Anica Markovac | Procede pour la preparation de 2-fluoro-9-(2,3,5-tri-o-benzyl-beta-d-arabinofuranosyl)adenine |
| US5532349A (en) * | 1993-07-20 | 1996-07-02 | Mitsui Toatsu Chemicals, Inc. | Process for producing 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-5-trifluoromethyluracil derivatives |
| DE19513330A1 (de) * | 1995-04-03 | 1996-10-10 | Schering Ag | Neues Verfahren zur Herstellung von Nucleosiden |
| JP2007522151A (ja) * | 2004-12-08 | 2007-08-09 | シコール インコーポレイティド | ジフルオロヌクレオシド及びその調製方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795357A1 (de) * | 1968-09-18 | 1972-01-05 | Schering Ag | 2-Thio-pyrimidin-nucleoside |
-
1970
- 1970-02-27 CH CH294970A patent/CH541566A/de not_active IP Right Cessation
- 1970-02-27 SU SU1410928A patent/SU452961A3/ru active
- 1970-04-03 DK DK168870AA patent/DK126198B/da unknown
- 1970-04-08 US US00026783A patent/US3748320A/en not_active Expired - Lifetime
- 1970-04-08 ES ES378367A patent/ES378367A1/es not_active Expired
- 1970-04-09 JP JP45030460A patent/JPS52955B1/ja active Pending
- 1970-04-09 SE SE04877/70A patent/SE363830B/xx unknown
- 1970-04-10 NO NO01327/70A patent/NO126322B/no unknown
- 1970-04-10 FR FR7012992A patent/FR2043174A5/fr not_active Expired
- 1970-04-10 FI FI1004/70A patent/FI54314C/fi active
- 1970-04-10 BE BE748799D patent/BE748799A/fr unknown
- 1970-04-10 IL IL34301A patent/IL34301A/en unknown
- 1970-04-10 AT AT330670A patent/AT315384B/de not_active IP Right Cessation
- 1970-04-10 PL PL1970139947A patent/PL93943B1/pl unknown
- 1970-04-11 NL NL7005235.A patent/NL166266B/xx not_active IP Right Cessation
- 1970-04-13 CA CA079967A patent/CA931948A/en not_active Expired
- 1970-04-13 IE IE475/70A patent/IE33786B1/xx unknown
- 1970-04-13 GB GB1744370A patent/GB1313411A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7005235A (fr) | 1970-10-13 |
| SE363830B (fr) | 1974-02-04 |
| IE33786L (en) | 1970-10-11 |
| NL166266B (nl) | 1981-02-16 |
| DK126198B (da) | 1973-06-18 |
| US3748320A (en) | 1973-07-24 |
| CH541566A (de) | 1973-09-15 |
| AT315384B (de) | 1974-05-27 |
| CA931948A (en) | 1973-08-14 |
| PL93943B1 (fr) | 1977-07-30 |
| SU452961A3 (ru) | 1974-12-05 |
| IL34301A0 (en) | 1970-06-17 |
| FI54314C (fi) | 1978-11-10 |
| IE33786B1 (en) | 1974-10-30 |
| JPS52955B1 (fr) | 1977-01-11 |
| BE748799A (fr) | 1970-10-12 |
| IL34301A (en) | 1973-06-29 |
| ES378367A1 (es) | 1972-06-16 |
| FR2043174A5 (fr) | 1971-02-12 |
| GB1313411A (en) | 1973-04-11 |
| FI54314B (fi) | 1978-07-31 |
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