تفاعل #3747

معادلة التفاعل

5'-O-(4,4'-dimethoxytrityl)thymidine

imidazole

tert-butyl-dimethylsilyl chloride

→

5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethlsilyl) thymidine

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىDMF was then removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 300 ml of ethyl acetate
3. 3
   غسيلThe solution was washed with water
4. 4
   تجفيفthe organic layer was dried over MgSO4
5. 5
   أخرىAfter concentration of the solution and recrystallization from ethyl acetate/hexane
6. 6
   أخرىthe solid product 5'-O-(4,4'-dimethoxy)-3'-(tert-butyldimethylsilyl)thymidine 17 was used directly for the next reaction

الإجراء التجريبي

To a solution of 13.0 g (23.9 mmol) 5'-O-(4,4'-dimethoxytrityl)thymidine 16 in 50 ml DMF was added 3.0 g (44 mmol) imidazole and 3.6 g (23.9 mmol) tert-butyl-dimethylsilyl chloride. The solution was stirred at room temperature for 3 hours. DMF was then removed in vacuo and the residue was dissolved in 300 ml of ethyl acetate. The solution was washed with water and the organic layer was dried over MgSO4. After concentration of the solution and recrystallization from ethyl acetate/hexane, the solid product 5'-O-(4,4'-dimethoxy)-3'-(tert-butyldimethylsilyl)thymidine 17 was used directly for the next reaction.

المصدر