Reacción #3747

Ecuación de reacción

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

imidazole

tert-butyl-dimethylsilyl chloride

→

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente