JPS6365077B2 - - Google Patents
Info
- Publication number
- JPS6365077B2 JPS6365077B2 JP9970981A JP9970981A JPS6365077B2 JP S6365077 B2 JPS6365077 B2 JP S6365077B2 JP 9970981 A JP9970981 A JP 9970981A JP 9970981 A JP9970981 A JP 9970981A JP S6365077 B2 JPS6365077 B2 JP S6365077B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- unsaturated
- nitrophenyl
- reaction
- hydrogen atom
- 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 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 125000003835 nucleoside group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002777 nucleoside Substances 0.000 description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000003212 purines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 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 2
- 150000003838 adenosines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- -1 2-nitrophenyl Chemical group 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 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
- 239000002126 C01EB10 - Adenosine Substances 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
- 229960000643 adenine Drugs 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 239000003905 agrochemical Substances 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
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000203 mixture Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9970981A JPS584780A (ja) | 1981-06-29 | 1981-06-29 | ４′，５′−不飽和ヌクレオシドの合成法 |
| 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 |
|---|---|---|---|
| JP9970981A JPS584780A (ja) | 1981-06-29 | 1981-06-29 | ４′，５′−不飽和ヌクレオシドの合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS584780A JPS584780A (ja) | 1983-01-11 |
| JPS6365077B2 true JPS6365077B2 (US07608600-20091027-C00048.png) | 1988-12-14 |
Family
ID=14254594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9970981A Granted JPS584780A (ja) | 1981-06-29 | 1981-06-29 | ４′，５′−不飽和ヌクレオシドの合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS584780A (US07608600-20091027-C00048.png) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047520A (en) * | 1987-03-19 | 1991-09-10 | Yamasa Shoyu Kabushiki Kaisha | 2'-alkylidenepyrimidine nucleoside derivatives, process for production thereof, and uses thereof |
-
1981
- 1981-06-29 JP JP9970981A patent/JPS584780A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS584780A (ja) | 1983-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6090932A (en) | Method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement | |
| US5763599A (en) | Nucleoside derivatives with photolabile protective groups | |
| EP1102782B1 (en) | Structural analogs of amine bases and nucleosides | |
| EP0521923B1 (en) | Process for producing nucleosides, and analogs therof | |
| JPS6139318B2 (US07608600-20091027-C00048.png) | ||
| JP2011001372A (ja) | イノシン誘導体及びその製造方法 | |
| AU711814B2 (en) | Nucleoside derivatives with photolabile protective groups | |
| JP2005504036A (ja) | プリンヌクレオシドを調製する方法 | |
| Dimitrijevich et al. | Halo sugar nucleosides. 6. Synthesis of some 5'-deoxy-5'-iodo and 4', 5'-unsaturated purine nucleosides | |
| JPS6365077B2 (US07608600-20091027-C00048.png) | ||
| Sasaki et al. | Introduction of a 2', 3'double bond into purine ribonucleosides by selective elimination reactions | |
| HU209310B (en) | Process for producing deoxynucleozides | |
| US4552955A (en) | Process for the synthesis of 4',5'-unsaturated nucleosides | |
| EP0523080B1 (en) | 2,3'-o-cyclocytidines, and process for production thereof | |
| JPS6365076B2 (US07608600-20091027-C00048.png) | ||
| JP4174895B2 (ja) | ヌクレオシド誘導体とその製法 | |
| JPH05271224A (ja) | 新規なオキセタン環含有ヌクレオシド誘導体 | |
| CA2012093C (en) | Process for producing 2,2'-cyclocytidine and analogues thereof | |
| WO2000039144A1 (fr) | Procede de preparation de derives fluores de nucleosides et de sucres | |
| JPH05320122A (ja) | オリゴヌクレオチドの化学的合成法 | |
| 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 | |
| JPS63264596A (ja) | ジデヒドロヌクレオシド類の製造方法 | |
| KR910005899B1 (ko) | 3'-데옥시 아라비노 프라노실 피리미딘 누클레오시드 유도체 | |
| JPH0665281A (ja) | ２−アミノ（２，３，５−トリ−０−ベンジル−β−Ｄ−アラビノフラノシル）アデニンの調製の改良方法 | |
| JPH02124897A (ja) | エリスロフラノシルヌクレオシド誘導体の製造法及び新規誘導体 |
