반응 #3747

반응 방정식

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

imidazole

tert-butyl-dimethylsilyl chloride

→

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

용매

DMF

반응 조건

후처리

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

실험 절차

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.

출처