RU96119766A - Производные 2,3-дидезоксипиримидина и диастереоселективный способ их получения - Google Patents
Производные 2,3-дидезоксипиримидина и диастереоселективный способ их полученияInfo
- Publication number
- RU96119766A RU96119766A RU96119766/04A RU96119766A RU96119766A RU 96119766 A RU96119766 A RU 96119766A RU 96119766/04 A RU96119766/04 A RU 96119766/04A RU 96119766 A RU96119766 A RU 96119766A RU 96119766 A RU96119766 A RU 96119766A
- Authority
- RU
- Russia
- Prior art keywords
- bromine
- iodine
- chlorine
- fluorine
- alkyl
- Prior art date
Links
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 6
- 239000011630 iodine Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000473 carbonimidoyl group Chemical group [H]\N=C(/*)* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000003899 glycosylation Effects 0.000 claims 1
- 238000006206 glycosylation reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Claims (2)
1. Производные 2,3-дидезоксипиримидина формулы VIII
где W - O, S, S=O, NZ или СН2;
X - O, S, S=O, SO2, NZ, СН2, CHF, CH, CHN3 или CHOH;
Y - О, S, СН2, CH, CHF или СНОН или СНОН;
Z - водород, гидроксил, алкил или ацил;
при условии, что когда Y - СН2 и X - О, S, S=О или SО2, то W не является О, S, S=O или SO2;
R2 - пуриновое или пиримидиновое основание или его аналог или его производное; и
R3 - замещенный карбонил или карбонильное производное.
где W - O, S, S=O, NZ или СН2;
X - O, S, S=O, SO2, NZ, СН2, CHF, CH, CHN3 или CHOH;
Y - О, S, СН2, CH, CHF или СНОН или СНОН;
Z - водород, гидроксил, алкил или ацил;
при условии, что когда Y - СН2 и X - О, S, S=О или SО2, то W не является О, S, S=O или SO2;
R2 - пуриновое или пиримидиновое основание или его аналог или его производное; и
R3 - замещенный карбонил или карбонильное производное.
2. Диастереоселективный способ получения цис-соединения формулы VIIIА
R2 - пуриновое или пиримидиновое основание или его аналог или производное;
R3 - замещенный карбонил или карбонильное производное;
W - S, S=О или SО2, О, NZ или СН2;
X - О, S, S=О или SO2, NZ, СН2, CHF, CH, CHN3 или СНОН;
Y - О, S, СН2, CH, CHF или СНОН; и
Z - водород, гидроксил, алкил или ацил;
при условии, что W - не О, S, S=О или SO2, когда Y - СН2 и Х - О, S, S=О или SO2,
отличающийся тем, что включает в себя стадию гликозилирования требуемого пуринового или пиримидинового основания или его аналога или производного соединением формулы II
где L - уходящая группа,
с использованием кислоты Льюиса формулы III
где R5, R6 и R7 независимо выбраны из группы, состоящей из водорода; С1-20 алкила, необязательно замещенного фтором, бромом, хлором, иодом, С1-6 алкокси или С6-20 арилокси; С7-20 аралкила, необязательно замещенного галогеном, С1-20 алкилом или С1-20 алкокси; С6-20 арила, необязательно замещенного фтором, бромом, хлором, иодом, С1-20 алкилом или С1-20 алкокси; триалкилсилила; фтора; брома; хлора и иода; и
R3 выбран из группы, состоящей из фтора; брома; хлора, иода; сложных эфиров С1-20 сульфокислоты, необязательно замещенных фтором, бромом, хлором или иодом; сложных С1-20 алкиловых эфиров, необязательно замещенных фтором, бромом, хлором или иодом; поливалентных галогенидов; трехзамещенных силильных групп общей формулы (R5) (R6) (R7)Si (где R5, R6 и R7 - такие, как определены выше); насыщенного или ненасыщенного селененил - С6-20 арила; замещенного или незамещенного С6-20 арилсульфенила; замещенного или незамещенного С6-20 алкоксиалкила; и триалкилсилокси.
R2 - пуриновое или пиримидиновое основание или его аналог или производное;
R3 - замещенный карбонил или карбонильное производное;
W - S, S=О или SО2, О, NZ или СН2;
X - О, S, S=О или SO2, NZ, СН2, CHF, CH, CHN3 или СНОН;
Y - О, S, СН2, CH, CHF или СНОН; и
Z - водород, гидроксил, алкил или ацил;
при условии, что W - не О, S, S=О или SO2, когда Y - СН2 и Х - О, S, S=О или SO2,
отличающийся тем, что включает в себя стадию гликозилирования требуемого пуринового или пиримидинового основания или его аналога или производного соединением формулы II
где L - уходящая группа,
с использованием кислоты Льюиса формулы III
где R5, R6 и R7 независимо выбраны из группы, состоящей из водорода; С1-20 алкила, необязательно замещенного фтором, бромом, хлором, иодом, С1-6 алкокси или С6-20 арилокси; С7-20 аралкила, необязательно замещенного галогеном, С1-20 алкилом или С1-20 алкокси; С6-20 арила, необязательно замещенного фтором, бромом, хлором, иодом, С1-20 алкилом или С1-20 алкокси; триалкилсилила; фтора; брома; хлора и иода; и
R3 выбран из группы, состоящей из фтора; брома; хлора, иода; сложных эфиров С1-20 сульфокислоты, необязательно замещенных фтором, бромом, хлором или иодом; сложных С1-20 алкиловых эфиров, необязательно замещенных фтором, бромом, хлором или иодом; поливалентных галогенидов; трехзамещенных силильных групп общей формулы (R5) (R6) (R7)Si (где R5, R6 и R7 - такие, как определены выше); насыщенного или ненасыщенного селененил - С6-20 арила; замещенного или незамещенного С6-20 арилсульфенила; замещенного или незамещенного С6-20 алкоксиалкила; и триалкилсилокси.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70337991A | 1991-05-21 | 1991-05-21 | |
| US703379 | 1991-05-21 | ||
| US703.379 | 1991-05-21 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93058554A Division RU2105009C1 (ru) | 1991-05-21 | 1992-05-20 | Способ диастереоселективного получения оптически активных цис-нуклеозидов, аналогов нуклеозидов или производных и промежуточные продукты для этого способа |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96119766A true RU96119766A (ru) | 1999-01-20 |
| RU2163909C2 RU2163909C2 (ru) | 2001-03-10 |
Family
ID=24825144
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99115480/04A RU2223960C2 (ru) | 1991-05-21 | 1992-05-20 | Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания |
| RU93058554A RU2105009C1 (ru) | 1991-05-21 | 1992-05-20 | Способ диастереоселективного получения оптически активных цис-нуклеозидов, аналогов нуклеозидов или производных и промежуточные продукты для этого способа |
| RU93058362A RU2140925C1 (ru) | 1991-05-21 | 1992-05-20 | Способы диастереоселективного синтеза нуклеозидов, промежуточные соединения, способы получения промежуточных соединений |
| RU96119766/04A RU2163909C2 (ru) | 1991-05-21 | 1992-05-20 | Производные пиримидиновых 2,3-дидезоксинуклеозидов и способ их получения |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99115480/04A RU2223960C2 (ru) | 1991-05-21 | 1992-05-20 | Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания |
| RU93058554A RU2105009C1 (ru) | 1991-05-21 | 1992-05-20 | Способ диастереоселективного получения оптически активных цис-нуклеозидов, аналогов нуклеозидов или производных и промежуточные продукты для этого способа |
| RU93058362A RU2140925C1 (ru) | 1991-05-21 | 1992-05-20 | Способы диастереоселективного синтеза нуклеозидов, промежуточные соединения, способы получения промежуточных соединений |
Country Status (34)
| Country | Link |
|---|---|
| US (5) | US5756706A (ru) |
| EP (2) | EP0515156B1 (ru) |
| JP (3) | JP3330972B2 (ru) |
| KR (3) | KR100232012B1 (ru) |
| CN (6) | CN1038591C (ru) |
| AT (2) | ATE133958T1 (ru) |
| AU (4) | AU1690892A (ru) |
| BG (2) | BG61696B1 (ru) |
| CA (2) | CA2069024C (ru) |
| CZ (3) | CZ284975B6 (ru) |
| DE (2) | DE69221936T2 (ru) |
| DK (2) | DK0515157T3 (ru) |
| EE (1) | EE03044B1 (ru) |
| ES (2) | ES2104832T3 (ru) |
| FI (3) | FI109025B (ru) |
| GR (2) | GR3018941T3 (ru) |
| GT (1) | GT199800047A (ru) |
| HK (2) | HK132196A (ru) |
| HU (2) | HU221850B1 (ru) |
| IE (2) | IE921618A1 (ru) |
| IL (6) | IL101931A (ru) |
| MD (1) | MD1155C2 (ru) |
| MX (2) | MX9202395A (ru) |
| NO (2) | NO301010B1 (ru) |
| NZ (2) | NZ242818A (ru) |
| OA (1) | OA10212A (ru) |
| PL (3) | PL176026B1 (ru) |
| RO (1) | RO116812B1 (ru) |
| RU (4) | RU2223960C2 (ru) |
| SG (1) | SG43863A1 (ru) |
| SK (2) | SK279438B6 (ru) |
| TW (4) | TW366350B (ru) |
| WO (2) | WO1992020669A1 (ru) |
| ZA (2) | ZA923640B (ru) |
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