JPS6244557B2 - - Google Patents
Info
- Publication number
- JPS6244557B2 JPS6244557B2 JP6640678A JP6640678A JPS6244557B2 JP S6244557 B2 JPS6244557 B2 JP S6244557B2 JP 6640678 A JP6640678 A JP 6640678A JP 6640678 A JP6640678 A JP 6640678A JP S6244557 B2 JPS6244557 B2 JP S6244557B2
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- dichloroethane
- reaction
- nucleoside
- tetrafluoroborate
- 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
- 239000002777 nucleoside Substances 0.000 claims description 21
- -1 triethyloxonium tetrafluoroborate Chemical compound 0.000 claims description 18
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 16
- 235000000346 sugar Nutrition 0.000 claims description 9
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 125000003835 nucleoside group Chemical group 0.000 description 5
- STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 3
- IEOLRPPTIGNUNP-RKQHYHRCSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O IEOLRPPTIGNUNP-RKQHYHRCSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- LJUQGASMPRMWIW-UHFFFAOYSA-N 5,6-dimethylbenzimidazole Chemical compound C1=C(C)C(C)=CC2=C1NC=N2 LJUQGASMPRMWIW-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CGEYLEQVYDREGR-BILGYAHESA-N [(2R,3R,4R,5S)-4,5-dibenzoyloxy-2-(hydroxymethyl)oxolan-3-yl] benzoate Chemical compound C(C1=CC=CC=C1)(=O)O[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](OC(C2=CC=CC=C2)=O)[C@H](O1)CO CGEYLEQVYDREGR-BILGYAHESA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003905 agrochemical Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6640678A JPS54157566A (en) | 1978-06-02 | 1978-06-02 | Preparation of nucleoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6640678A JPS54157566A (en) | 1978-06-02 | 1978-06-02 | Preparation of nucleoside |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54157566A JPS54157566A (en) | 1979-12-12 |
| JPS6244557B2 true JPS6244557B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-09-21 |
Family
ID=13314877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6640678A Granted JPS54157566A (en) | 1978-06-02 | 1978-06-02 | Preparation of nucleoside |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54157566A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230044958A (ko) * | 2021-09-27 | 2023-04-04 | 한양대학교 에리카산학협력단 | 전자 소자 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111961380A (zh) * | 2020-07-25 | 2020-11-20 | 候伟强 | 一种家居水性涂料及其制备方法 |
-
1978
- 1978-06-02 JP JP6640678A patent/JPS54157566A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230044958A (ko) * | 2021-09-27 | 2023-04-04 | 한양대학교 에리카산학협력단 | 전자 소자 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54157566A (en) | 1979-12-12 |
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