Reaktion #51525

Reaktionsgleichung

NaH

(2-bromo ethyl)-tert-butyldimethylsilane

Adenosine

P2O5

→

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

Lösungsmittel

DMF

CH2Cl2

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature overnight
2. 2
   SonstigeDMF was removed under vacuum and to the residue dichloromethane (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   Waschenwashed with water (2×80 mL)
5. 5
   TrocknenDichloromethane layer was dried over anhydrous Na2SO4
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeResidue purified by column
8. 8
   Sonstigeto get

Vorschrift

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)

Quelle