RU2223960C2 - Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания - Google Patents

Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания Download PDF

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RU2223960C2
RU2223960C2 RU99115480/04A RU99115480A RU2223960C2 RU 2223960 C2 RU2223960 C2 RU 2223960C2 RU 99115480/04 A RU99115480/04 A RU 99115480/04A RU 99115480 A RU99115480 A RU 99115480A RU 2223960 C2 RU2223960 C2 RU 2223960C2
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Тарек МАНСУР (CA)
Тарек Мансур
Хаолун ДЖИН (CN)
Хаолун Джин
Аллан Х.Л. ТСЕ (GB)
Аллан Х.Л. ТСЕ
М.Аршад СИДДИКИ (IN)
М.Аршад СИДДИКИ
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Abstract

Способ по изобретению включает гликозилирование силилированого пуринового или пиримидинового основания, или его аналога или производного соединением формулы (IIа) или (IIв), где R3 - замещенный карбонил или карбонильное производное, W и Х - это S, S=О, SO2 или О, L - уходящая группа, с использованием кислоты Льюиса формулы (III) (значения радикалов R5-R8 см. в описании). В другом варианте осуществления способа указанные основания, их аналоги или производные подвергают гликозилированию одиночным энантиомером расщепленного сложного эфира, полученного из соединения формулы (IX), в присутствии кислоты Льюиса формулы (III). Технический результат - повышение оптической чистоты целевых продуктов. 2 с. и 15 з.п. ф-лы.
Figure 00000001

Figure 00000002

Figure 00000003

Description

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Claims (17)

1. Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания, или его аналога, или производного, заключающийся в том, что силилированное пуриновое или силилированное пиримидиновое основание, или его аналог, или производное подвергают гликозилированию соединением формулы (IIа) или (IIв)
Figure 00000109
где R3 - замещенный карбонил или карбонильное производное;
L - уходящая группа,
с использованием кислоты Льюиса формулы (III)
Figure 00000110
где R5, R6 и R7 независимо выбраны из группы, состоящей из водорода; C1-20алкила, необязательно замещенного фтором, бромом, хлором, иодом, С1-6алкокси или С6-20арилокси; С7-20аралкила, необязательно замещенного галогеном, C1-20алкилом или C1-20алкокси; C6-20арила, необязательно замещенного фтором, бромом, хлором, иодом, C1-20алкилом или C1-20алкокси; триалкилсилила, фтора, брома, хлора и иода,
R8 - выбран из группы, состоящей из фтора, брома, хлора, иода; сложных эфиров C1-20сульфокислоты, необязательно замещенных фтором, бромом, хлором или иодом; сложных C1-20алкиловых эфиров, необязательно замещенных фтором, бромом, хлором или иодом; трийодида; силильной группы общей формулы (R5), (R6), (R7) Si (где R5 R6 R7 - такие, как определены выше); С6-20арилселененила, С6-20арилсульфенила, С6-20алкоксиалкила и триалкилсилокси;
W - S, S=O, SO2 или О;
Х - S, S=O, SO2 или О.
2. Способ по п.1, отличающийся тем, что соединение формулы (IIа) или (IIb) получают путем химического выделения упомянутого соединения из смеси (IIа) и (IIb) с использованием хирального вспомогательного реагента.
3. Способ по п.1, отличающийся тем, что используют соединение формулы (IIа).
4. Способ по п.1, отличающийся тем, что используют соединение формулы (IIb).
5. Способ по п.1, отличающийся тем, что соединение формулы (IIа) и (IIb) выбирают из группы, состоящей из
Figure 00000111
6. Способ по п.1, отличающийся тем, что гликолизируют пиримидиновое основание.
7. Способ по п.6, отличающийся тем, что пиримидиновым основанием является цитозин или 5-фторцитозин.
8. Способ по п.1, отличающийся тем, что кислоту Льюиса выбирают из группы, состоящей из триметилсилилтрифлата и иодтриметилсилана.
9. Способ по п.2, отличающийся тем, что хиральный вспомогательный реагент выбирают из группы, состоящей из хиральных спиртов и хиральных аминов.
10. Способ по п.9, отличающийся тем, что хиральный вспомогательный агент выбирают из группы, состоящей из (d)-ментола, (I)-ментола, (+)-норэфедрина и (-)-норэфедрина.
11. Способ по п.1, отличающийся тем, что R3 выбирают из группы, состоящей из алкоксикарбонила, карбоксила, диэтилкарбоксамида, пирролидинамида, метилкетона и фенилкетона.
12. Способ по п.11, отличающийся тем, что R3 выбирают из группы, состоящей из алкоксикарбонила и карбоксила.
13. Диастероселективный способ получения гликозилированного пуринового или пиримидинового основания, или его аналога, или производного, заключающийся в том, что силилированное пуриновое или силилированное пиримидиновое основание, или его аналог, или производное подвергают гликозилированию одиночным энантиомером расщепленного сложного эфира, полученного из соединения формулы (IX)
Figure 00000112
с использованием кислоты Льюиса формулы (III)
Figure 00000113
где R5 R6 и R7 независимо выбраны из группы, состоящей из водорода; C1-20алкила, необязательно замещенного фтором, бромом, хлором, иодом, C1-6алкокси или С6-20арилокси; C7-20аралкила, необязательно замещенного галогеном, C1-20алкилом или C1-20алкокси, C6-20арила, необязательно замещенного фтором, бромом, хлором, иодом, C1-20алкилом или C1-20алкокси; триалкилсилила, фтора, брома, хлора и иода;
R8 выбран из группы, состоящей из фтора, брома, хлора, иода, сложных эфиром C1-20сульфокислоты, необязательно замещенных фтором, бромом, хлором или иодом; сложных C1-20алкиловых эфиров, необязательно замещенных фтором, бромом, хлором или иодом; трийодида, силильной группы общей формулы (R5) (R6) (R7) Si (где R5, R6 и R7 - такие, как определены выше), С6-20арилселененила, С6-20арилсульфенила, С6-20алкоксиалкила и триалкилсилокси.
14. Способ по п.13, отличающийся тем, что одиночный энантиомер сложного эфира получают из соединения формулы (IX) с использованием хирального вспомогательного реагента.
15. Способ по п.14, отличающийся тем, что хиральный вспомогательный реагент выбирают из группы, состоящей из (d)-ментола и (I)-ментола.
16. Способ по п.13, отличающийся тем, что гликолизируют пиримидиновое основание.
17. Способ по п.16, отличающийся тем, что пиримидиновым основанием является цитозин или 5-фторцитозин.
RU99115480/04A 1991-05-21 1992-05-20 Диастереоселективный способ получения гликозилированного пуринового или пиримидинового основания RU2223960C2 (ru)

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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

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RU93058362A RU2140925C1 (ru) 1991-05-21 1992-05-20 Способы диастереоселективного синтеза нуклеозидов, промежуточные соединения, способы получения промежуточных соединений

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