JPS60120890A - 新規ホスホリル化剤 - Google Patents
新規ホスホリル化剤Info
- Publication number
- JPS60120890A JPS60120890A JP22839583A JP22839583A JPS60120890A JP S60120890 A JPS60120890 A JP S60120890A JP 22839583 A JP22839583 A JP 22839583A JP 22839583 A JP22839583 A JP 22839583A JP S60120890 A JPS60120890 A JP S60120890A
- Authority
- JP
- Japan
- Prior art keywords
- nucleoside
- formula
- compound
- reacting
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000006366 phosphorylation reaction Methods 0.000 title abstract description 9
- 230000026731 phosphorylation Effects 0.000 title abstract description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004020 conductor Substances 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 239000000047 product Substances 0.000 abstract description 8
- 229910019142 PO4 Inorganic materials 0.000 abstract description 6
- 239000010452 phosphate Substances 0.000 abstract description 6
- JWKMDCBKGBDVKK-HFASVGIHSA-N 1-[(2s,4s,5r)-4-hydroxy-5-(methylperoxymethyl)-2-trityloxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](COOC)O[C@@]1(C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1C(=O)NC(=O)C(C)=C1 JWKMDCBKGBDVKK-HFASVGIHSA-N 0.000 abstract description 5
- -1 phosphate compound Chemical class 0.000 abstract description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 abstract description 2
- IESPNWVSLUTLPN-UHFFFAOYSA-N bis(2,2,2-trifluoroethyl) phosphite Chemical compound FC(F)(F)COP([O-])OCC(F)(F)F IESPNWVSLUTLPN-UHFFFAOYSA-N 0.000 abstract description 2
- 150000007523 nucleic acids Chemical class 0.000 abstract description 2
- 102000039446 nucleic acids Human genes 0.000 abstract description 2
- 108020004707 nucleic acids Proteins 0.000 abstract description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000000865 phosphorylative effect Effects 0.000 description 7
- 238000007086 side reaction Methods 0.000 description 5
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 4
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 2
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 2
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 2
- 229940029575 guanosine Drugs 0.000 description 2
- 125000003835 nucleoside group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
- 229940045145 uridine Drugs 0.000 description 2
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- NIPKRLLKGZROTE-UHFFFAOYSA-N 4-methoxy-n-(2-oxo-1h-pyrimidin-6-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=NC(=O)NC=C1 NIPKRLLKGZROTE-UHFFFAOYSA-N 0.000 description 1
- OOLRAQKFMNOZBV-UHFFFAOYSA-N 8-n-[(4-aminophenyl)methyl]-3,6,10,13,16,19-hexazabicyclo[6.6.6]icosane-1,8-diamine Chemical compound C1=CC(N)=CC=C1CNC1(CNCCNC2)CNCCNCC2(N)CNCCNC1 OOLRAQKFMNOZBV-UHFFFAOYSA-N 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100170604 Mus musculus Dmap1 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- RZCVPJDHJYOZNP-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)benzamide Chemical compound N=1C(=O)C=2NC=NC=2NC=1NC(=O)C1=CC=CC=C1 RZCVPJDHJYOZNP-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102220043690 rs1049562 Human genes 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22839583A JPS60120890A (ja) | 1983-12-05 | 1983-12-05 | 新規ホスホリル化剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22839583A JPS60120890A (ja) | 1983-12-05 | 1983-12-05 | 新規ホスホリル化剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60120890A true JPS60120890A (ja) | 1985-06-28 |
| JPH0372235B2 JPH0372235B2 (enrdf_load_stackoverflow) | 1991-11-18 |
Family
ID=16875793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22839583A Granted JPS60120890A (ja) | 1983-12-05 | 1983-12-05 | 新規ホスホリル化剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60120890A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291088A (ja) * | 1988-09-29 | 1990-03-30 | Central Glass Co Ltd | ホスファイトおよびヌクレオシド‐３’‐ホスファイト誘導体およびこれを用いるオリゴヌクレオチドの合成法 |
| JPH0594874U (ja) * | 1992-05-15 | 1993-12-24 | 桜井株式会社 | 控え付きラベル |
-
1983
- 1983-12-05 JP JP22839583A patent/JPS60120890A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291088A (ja) * | 1988-09-29 | 1990-03-30 | Central Glass Co Ltd | ホスファイトおよびヌクレオシド‐３’‐ホスファイト誘導体およびこれを用いるオリゴヌクレオチドの合成法 |
| JPH0594874U (ja) * | 1992-05-15 | 1993-12-24 | 桜井株式会社 | 控え付きラベル |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0372235B2 (enrdf_load_stackoverflow) | 1991-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |