NO127236B - - Google Patents
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- Publication number
- NO127236B NO127236B NO7770A NO7770A NO127236B NO 127236 B NO127236 B NO 127236B NO 7770 A NO7770 A NO 7770A NO 7770 A NO7770 A NO 7770A NO 127236 B NO127236 B NO 127236B
- Authority
- NO
- Norway
- Prior art keywords
- benzene
- solution
- thio
- evaporated
- acetic acid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 19
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 claims description 18
- -1 trimethylsilylamino Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 8
- 235000000346 sugar Nutrition 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000002777 nucleoside Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 22
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 150000002168 ethanoic acid esters Chemical class 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000005051 trimethylchlorosilane Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PUZXBTLFTSXRJX-LLNWNZGGSA-N [(2r,3r,4r)-3,4-dibenzoyloxy-5-chloro-5-hydroxyoxolan-2-yl]methyl benzoate Chemical compound C([C@H]1OC([C@@H]([C@@H]1OC(=O)C=1C=CC=CC=1)OC(=O)C=1C=CC=CC=1)(Cl)O)OC(=O)C1=CC=CC=C1 PUZXBTLFTSXRJX-LLNWNZGGSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical group [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- GIYNGEREYFQLSB-VNSJUHMKSA-N C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=S)N=C(N)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=S)N=C(N)C=C1 GIYNGEREYFQLSB-VNSJUHMKSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- YGLNFSXTZCTXPQ-UHFFFAOYSA-N trimethyl-(5-methyl-4-trimethylsilyloxypyrimidin-2-yl)sulfanylsilane Chemical compound CC1=CN=C(S[Si](C)(C)C)N=C1O[Si](C)(C)C YGLNFSXTZCTXPQ-UHFFFAOYSA-N 0.000 description 3
- UOACTXXMBOYUMC-UHFFFAOYSA-N (5-ethyl-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane Chemical compound CCC1=CN=C(S[Si](C)(C)C)N=C1O[Si](C)(C)C UOACTXXMBOYUMC-UHFFFAOYSA-N 0.000 description 2
- JVORBOVNEPOGJJ-UHFFFAOYSA-N (5-methoxy-4-trimethylsilyloxypyrimidin-2-yl)sulfanyl-trimethylsilane Chemical compound COC1=CN=C(S[Si](C)(C)C)N=C1O[Si](C)(C)C JVORBOVNEPOGJJ-UHFFFAOYSA-N 0.000 description 2
- JUMHLCXWYQVTLL-KVTDHHQDSA-N 2-thio-5-aza-uridine Chemical compound [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=S)NC(=O)N=C1 JUMHLCXWYQVTLL-KVTDHHQDSA-N 0.000 description 2
- RHFUOMFWUGWKKO-XVFCMESISA-N 2-thiocytidine Chemical compound S=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RHFUOMFWUGWKKO-XVFCMESISA-N 0.000 description 2
- CDFYFTSELDPCJA-UHFFFAOYSA-N 5-methoxy-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound COC1=CNC(=S)NC1=O CDFYFTSELDPCJA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- RVMRMDZZVKDUOU-DLGLWYJGSA-N [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(5-methoxy-4-oxo-2-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=S)NC(=O)C(=C1)OC RVMRMDZZVKDUOU-DLGLWYJGSA-N 0.000 description 2
- ZAHOZJCQNRXDIV-VNSJUHMKSA-N [(2r,3r,4r,5r)-3,4-dibenzoyloxy-5-(4-oxo-2-sulfanylidenepyrimidin-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)=S)C(=O)C1=CC=CC=C1 ZAHOZJCQNRXDIV-VNSJUHMKSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- AJYVYADCXGPPML-QIPHTDNOSA-N benzoic acid ethyl 2-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-oxo-2-sulfanylidenepyrimidin-5-yl]acetate Chemical compound C(C1=CC=CC=C1)(=O)O.C(C1=CC=CC=C1)(=O)O.C(C1=CC=CC=C1)(=O)O.C(C)OC(CC=1C(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C1)=S)=O)=O AJYVYADCXGPPML-QIPHTDNOSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IQKSHKCJKQQMLH-UHFFFAOYSA-N n-trimethylsilyl-2-trimethylsilylsulfanylpyrimidin-4-amine Chemical compound C[Si](C)(C)NC1=CC=NC(S[Si](C)(C)C)=N1 IQKSHKCJKQQMLH-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002718 pyrimidine nucleoside Substances 0.000 description 2
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- RHFUOMFWUGWKKO-UHFFFAOYSA-N s2C Natural products S=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 RHFUOMFWUGWKKO-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CPULVOVSDZNOPC-UHFFFAOYSA-N trimethyl-(4-trimethylsilyloxypyrimidin-2-yl)sulfanylsilane Chemical compound C[Si](C)(C)OC1=CC=NC(S[Si](C)(C)C)=N1 CPULVOVSDZNOPC-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- UEDBWEAKPIIMDA-JXOAFFINSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methoxy-2-sulfanylidenepyrimidin-4-one Chemical compound S=C1NC(=O)C(OC)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 UEDBWEAKPIIMDA-JXOAFFINSA-N 0.000 description 1
- PISWNSOQFZRVJK-XLPZGREQSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-sulfanylidenepyrimidin-4-one Chemical compound S=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 PISWNSOQFZRVJK-XLPZGREQSA-N 0.000 description 1
- TVCBDTCUOVDLNZ-SHUUEZRQSA-N 2-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-sulfanylidene-1,2,4-triazin-5-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=S)NC(=O)C=N1 TVCBDTCUOVDLNZ-SHUUEZRQSA-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
- GJTBSTBJLVYKAU-XVFCMESISA-N 2-thiouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=S)NC(=O)C=C1 GJTBSTBJLVYKAU-XVFCMESISA-N 0.000 description 1
- HZPZCLDCTLLJTF-UHFFFAOYSA-N 3-sulfanylidene-2h-1,2,4-triazin-5-one Chemical compound O=C1C=NNC(=S)N1 HZPZCLDCTLLJTF-UHFFFAOYSA-N 0.000 description 1
- CMSWHQPRQCFYNR-UHFFFAOYSA-N 4-(trimethylsilylamino)-2-trimethylsilylsulfanylpyrimidine-5-carbonitrile Chemical compound C[Si](C)(C)NC1=NC(S[Si](C)(C)C)=NC=C1C#N CMSWHQPRQCFYNR-UHFFFAOYSA-N 0.000 description 1
- JYBWJPAOAQCXAX-UHFFFAOYSA-N 5-ethyl-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CCC1=CNC(=S)NC1=O JYBWJPAOAQCXAX-UHFFFAOYSA-N 0.000 description 1
- HLZXTFWTDIBXDF-PNHWDRBUSA-N 5-methoxycarbonylmethyl-2-thiouridine Chemical compound S=C1NC(=O)C(CC(=O)OC)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HLZXTFWTDIBXDF-PNHWDRBUSA-N 0.000 description 1
- ZLAQATDNGLKIEV-UHFFFAOYSA-N 5-methyl-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CC1=CNC(=S)NC1=O ZLAQATDNGLKIEV-UHFFFAOYSA-N 0.000 description 1
- DCPSTSVLRXOYGS-UHFFFAOYSA-N 6-amino-1h-pyrimidine-2-thione Chemical compound NC1=CC=NC(S)=N1 DCPSTSVLRXOYGS-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- OGYOVLCPDREHCC-UHFFFAOYSA-N C(C)OC(CC=1C(=NC(=NC=1)S[Si](C)(C)C)O[Si](C)(C)C)=O Chemical compound C(C)OC(CC=1C(=NC(=NC=1)S[Si](C)(C)C)O[Si](C)(C)C)=O OGYOVLCPDREHCC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RGCMQLOYEKOIFJ-PJJZGAISSA-N ClC1(O)[C@](O)([C@](O)([C@H](O1)C(O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O Chemical compound ClC1(O)[C@](O)([C@](O)([C@H](O1)C(O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O)C(C1=CC=CC=C1)=O RGCMQLOYEKOIFJ-PJJZGAISSA-N 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
- 238000003458 Hilbert-Johnson synthesis reaction Methods 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
- QRMHDGWGLNLHMN-UHFFFAOYSA-N Methyl methoxyacetate Chemical compound COCC(=O)OC QRMHDGWGLNLHMN-UHFFFAOYSA-N 0.000 description 1
- 229930182473 O-glycoside Natural products 0.000 description 1
- 150000008444 O-glycosides Chemical class 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001476 alcoholic effect Effects 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
- 125000003368 amide group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- NQOIPEBCWBNSJS-UHFFFAOYSA-N benzoyl chloride;pyridine Chemical compound C1=CC=NC=C1.ClC(=O)C1=CC=CC=C1 NQOIPEBCWBNSJS-UHFFFAOYSA-N 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
- 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
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- AZQJLAUOZFTBTH-UHFFFAOYSA-N ethyl 2-(4-oxo-2-sulfanylidene-1h-pyrimidin-5-yl)acetate Chemical compound CCOC(=O)CC1=CNC(=S)NC1=O AZQJLAUOZFTBTH-UHFFFAOYSA-N 0.000 description 1
- OFBNJEUAEZLKHY-UHFFFAOYSA-N ethyl 2-methoxy-3-oxopropanoate Chemical compound CCOC(=O)C(OC)C=O OFBNJEUAEZLKHY-UHFFFAOYSA-N 0.000 description 1
- VKZJJPNSXDYAMY-UHFFFAOYSA-N ethyl 4-(trimethylsilylamino)-2-trimethylsilylsulfanylpyrimidine-5-carboxylate Chemical compound C[Si](SC1=NC=C(C(=N1)N[Si](C)(C)C)C(=O)OCC)(C)C VKZJJPNSXDYAMY-UHFFFAOYSA-N 0.000 description 1
- VYLMLIMEMUJDEB-FDDDBJFASA-N ethyl 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-sulfanylidenepyrimidine-5-carboxylate Chemical compound C(=O)(OCC)C=1C(=NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)C=1)=S)N VYLMLIMEMUJDEB-FDDDBJFASA-N 0.000 description 1
- DKTWKRWWQKVQQB-UHFFFAOYSA-N ethyl 6-amino-2-sulfanylidene-1h-pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(S)N=C1N DKTWKRWWQKVQQB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- VOCGXRYDFYRGQI-UHFFFAOYSA-N trimethyl-[(5-trimethylsilyloxy-1,2,4-triazin-3-yl)sulfanyl]silane Chemical compound C[Si](C)(C)OC1=CN=NC(S[Si](C)(C)C)=N1 VOCGXRYDFYRGQI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO7770A NO127236B (enrdf_load_stackoverflow) | 1970-01-09 | 1970-01-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO7770A NO127236B (enrdf_load_stackoverflow) | 1970-01-09 | 1970-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127236B true NO127236B (enrdf_load_stackoverflow) | 1973-05-28 |
Family
ID=19877350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO7770A NO127236B (enrdf_load_stackoverflow) | 1970-01-09 | 1970-01-09 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO127236B (enrdf_load_stackoverflow) |
-
1970
- 1970-01-09 NO NO7770A patent/NO127236B/no unknown
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