JPS6365076B2 - - Google Patents
Info
- Publication number
- JPS6365076B2 JPS6365076B2 JP9970881A JP9970881A JPS6365076B2 JP S6365076 B2 JPS6365076 B2 JP S6365076B2 JP 9970881 A JP9970881 A JP 9970881A JP 9970881 A JP9970881 A JP 9970881A JP S6365076 B2 JPS6365076 B2 JP S6365076B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- nitrophenyl
- hydrogen atom
- substituent
- group
- 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.)
- Expired
Links
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- LHBLJWULWKQRON-UHFFFAOYSA-N (2-nitrophenyl) selenocyanate Chemical compound [O-][N+](=O)C1=CC=CC=C1[Se]C#N LHBLJWULWKQRON-UHFFFAOYSA-N 0.000 claims description 5
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 claims description 5
- 150000003230 pyrimidines Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000003835 nucleoside group Chemical group 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003212 purines Chemical class 0.000 description 3
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 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 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 150000003838 adenosines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- -1 2-nitrophenylseleno group Chemical group 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- UZSSGAOAYPICBZ-SOCHQFKDSA-N Decoyinine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@]1(CO)OC(=C)[C@@H](O)[C@H]1O UZSSGAOAYPICBZ-SOCHQFKDSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- UZSSGAOAYPICBZ-UHFFFAOYSA-N angustmycin A Natural products C1=NC=2C(N)=NC=NC=2N1C1(CO)OC(=C)C(O)C1O UZSSGAOAYPICBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9970881A JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
| US06/393,254 US4552955A (en) | 1981-06-29 | 1982-06-29 | Process for the synthesis of 4',5'-unsaturated nucleosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9970881A JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS584797A JPS584797A (ja) | 1983-01-11 |
| JPS6365076B2 true JPS6365076B2 (de) | 1988-12-14 |
Family
ID=14254562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9970881A Granted JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS584797A (de) |
-
1981
- 1981-06-29 JP JP9970881A patent/JPS584797A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS584797A (ja) | 1983-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5763599A (en) | Nucleoside derivatives with photolabile protective groups | |
| JP3653292B2 (ja) | ５−メチルウリジンを用いる２’，３’−ジデヒドロ−３’−デオキシチミジン（ｄ４Ｔ）の大量製造法 | |
| JP2011001372A (ja) | イノシン誘導体及びその製造方法 | |
| EP1412369B1 (de) | Verfahren zur herstellung von purinnukleosiden | |
| US6153744A (en) | Nucleoside derivatives with photolabile protective groups | |
| EP0351126B1 (de) | Verfahren zur Herstellung von O2,2'-anhydro-1-(beta-D-arabinofuranosyl)Thymin | |
| JPS6365076B2 (de) | ||
| HU209310B (en) | Process for producing deoxynucleozides | |
| US5821367A (en) | Regiospecific process for synthesis of acyclic nucleosides | |
| US5536824A (en) | Organosulfonyl salts of 2,3'-O-cyclocytidine | |
| US4552955A (en) | Process for the synthesis of 4',5'-unsaturated nucleosides | |
| JPS6365077B2 (de) | ||
| JPH05271224A (ja) | 新規なオキセタン環含有ヌクレオシド誘導体 | |
| JP3499896B2 (ja) | ２’−デオキシヌクレオシド類の製造方法 | |
| JP3527255B2 (ja) | ６−ｎ−置換アミノピコリン酸誘導体及びその製造法 | |
| JP2547125B2 (ja) | ２’，３’−ジデオキシ−２’，３’−ジ置換−ヌクレオシド類とその製造方法 | |
| JPH10130245A (ja) | アシクロヌクレオシドの製造方法 | |
| JPH05320122A (ja) | オリゴヌクレオチドの化学的合成法 | |
| WO2010079813A1 (ja) | イノシン誘導体の製造方法 | |
| JPH0296589A (ja) | ヌクレオシド類 | |
| JPH03264582A (ja) | ２’，３’―ジデオキシ―２’，３’―ジ置換―ヌクレオシド類とその製造方法 | |
| HU198949B (en) | Process for producing 5-substituted-3'azido-2',3'-dideoxyribonucleosides | |
| JP2001226394A (ja) | ２’−デオキシ−β−グアノシンの製造法およびその中間体 | |
| JPS5982396A (ja) | ５―置換ウラシルヌクレオシドの製造法 | |
| JPH02160799A (ja) | ２′−デオキシ−β−アデノシンの製造法 |