Réaction #3747

Équation de réaction

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

imidazole

tert-butyl-dimethylsilyl chloride

→

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

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source