反応 #51525

反応方程式

NaH

(2-bromo ethyl)-tert-butyldimethylsilane

Adenosine

P2O5

→

3′-O (2-tert-butyldimethylsilylhydroxyethyl)adenosine

溶媒

DMF

CH2Cl2

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature overnight
2. 2
   その他DMF was removed under vacuum and to the residue dichloromethane (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   洗浄washed with water (2×80 mL)
5. 5
   乾燥Dichloromethane layer was dried over anhydrous Na2SO4
6. 6
   その他evaporated to dryness
7. 7
   その他Residue purified by column
8. 8
   その他to get

実験手順

Adenosine (10 g, 37.42 mmol) was dried over P2O5 under high vacuum. It was then suspended in anhydrous DMF (150 mL) and NaH (1.35 g, 56.13 mmol) was added. The reaction mixture was stirred at room temperature under inert atmosphere for 30 min. Then (2-bromo ethyl)-tert-butyldimethylsilane (9.68 mL, 4.4.90 mmol) was added dropwise and the reaction mixture stirred at room temperature overnight. DMF was removed under vacuum and to the residue dichloromethane (100 mL) was added and washed with water (2×80 mL). Dichloromethane layer was dried over anhydrous Na2SO4 and evaporated to dryness. Residue purified by column to get a mixture of the title compounds (4.30 g). Rf 0.49, 0.57 (10% MeOH in CH2Cl2)

出典