RU96119766A - DERIVATIVES 2,3-DIDEOXYPYRIMIDINE AND DIASTERI-SELECTIVE WAY OF OBTAINING THEM - Google Patents

DERIVATIVES 2,3-DIDEOXYPYRIMIDINE AND DIASTERI-SELECTIVE WAY OF OBTAINING THEM

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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
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Russia
Prior art keywords
bromine
iodine
chlorine
fluorine
alkyl
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RU96119766/04A
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Russian (ru)
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RU2163909C2 (en
Inventor
Мансур Тарек
Х.Л.Тсе Аллан
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Биокем Фарма Инк.
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Publication of RU96119766A publication Critical patent/RU96119766A/en
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Claims (2)

1. Производные 2,3-дидезоксипиримидина формулы VIII
Figure 00000001

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.1. Derivatives of 2,3-dideoxypyrimidine of the formula VIII
Figure 00000001

where W is O, S, S = O, NZ or CH 2 ;
X is O, S, S = O, SO 2 , NZ, CH 2 , CHF, CH, CHN 3 or CHOH;
Y is O, S, CH 2 , CH, CHF or CHOH or CHOH;
Z is hydrogen, hydroxyl, alkyl or acyl;
provided that when Y is CH 2 and X is O, S, S = O or SO 2 , then W is not O, S, S = O or SO 2 ;
R 2 is a purine or pyrimidine base or an analog or derivative thereof; and
R 3 is a substituted carbonyl or carbonyl derivative. 2. Диастереоселективный способ получения цис-соединения формулы VIIIА
Figure 00000002

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
Figure 00000003

где L - уходящая группа,
с использованием кислоты Льюиса формулы III
Figure 00000004

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.2. Diastereoselective method of obtaining cis compounds of formula VIIIA
Figure 00000002

R 2 is a purine or pyrimidine base or an analog or derivative thereof;
R 3 is a substituted carbonyl or carbonyl derivative;
W is S, S = O or SO 2 , O, NZ or CH 2 ;
X is O, S, S = O or SO 2 , NZ, CH 2 , CHF, CH, CHN 3 or CHOH;
Y is O, S, CH 2 , CH, CHF or CHOH; and
Z is hydrogen, hydroxyl, alkyl or acyl;
provided that W is not O, S, S = O or SO 2 , when Y is CH 2 and X is O, S, S = O or SO 2 ,
characterized in that it comprises the step of glycosylation of the desired purine or pyrimidine base or its analogue or derivative with a compound of formula II
Figure 00000003

where L is a leaving group,
using Lewis acid of formula III
Figure 00000004

where R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen; C 1-20 alkyl, optionally substituted by fluorine, bromine, chlorine, iodine, C 1-6 alkoxy or C 6-20 aryloxy; C 7-20 aralkyl, optionally substituted with halogen, C 1-20 alkyl or C 1-20 alkoxy; C 6-20 aryl, optionally substituted with fluorine, bromine, chlorine, iodine, C 1-20 alkyl or C 1-20 alkoxy; trialkylsilyl; fluorine; bromine; chlorine and iodine; and
R 3 is selected from the group consisting of fluorine; bromine; chlorine, iodine; C 1-20 esters of sulfonic acids, optionally substituted by fluorine, bromine, chlorine or iodine; C 1-20 alkyl esters, optionally substituted with fluorine, bromine, chlorine or iodine; polyvalent halides; trisubstituted silyl groups of the general formula (R 5 ) (R 6 ) (R 7 ) Si (wherein R 5 , R 6 and R 7 are as defined above); saturated or unsaturated selenenyl — C 6-20 aryl; substituted or unsubstituted C 6-20 arylsulfenyl; substituted or unsubstituted C 6-20 alkoxyalkyl; and trialkylsiloxy.
RU96119766/04A 1991-05-21 1992-05-20 Pyrimidine 2,3-didesoxynucleoside derivatives and method of preparing thereof RU2163909C2 (en)

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RU99115480/04A RU2223960C2 (en) 1991-05-21 1992-05-20 Diastereoselective method for preparing glycosylated purine or pyrimidine base
RU93058554A RU2105009C1 (en) 1991-05-21 1992-05-20 Method of diastereoselective synthesis of optically active cis-nucleosides, nucleoside analogs or derivatives and intermediate compounds for this method
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RU93058362A RU2140925C1 (en) 1991-05-21 1992-05-20 Method of diastereoselective synthesis of nucleosides, intermediate compounds, and method of preparing intermediate compounds

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