Reaktion #3747

Reaktionsgleichung

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

imidazole

tert-butyl-dimethylsilyl chloride

→

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle