Reacción #51525

Ecuación de reacción

NaH

(2-bromo ethyl)-tert-butyldimethylsilane

Adenosine

P2O5

→

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

Disolventes

DMF

CH2Cl2

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature overnight
2. 2
   OtroDMF was removed under vacuum and to the residue dichloromethane (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   Lavadowashed with water (2×80 mL)
5. 5
   SecadoDichloromethane layer was dried over anhydrous Na2SO4
6. 6
   Otroevaporated to dryness
7. 7
   OtroResidue purified by column
8. 8
   Otroto get

Procedimiento

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)

Fuente