Реакция #51525

Уравнение реакции

NaH

(2-bromo ethyl)-tert-butyldimethylsilane

Adenosine

P2O5

→

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

Растворители

DMF

CH2Cl2

MeOH

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature overnight
2. 2
   ДругоеDMF was removed under vacuum and to the residue dichloromethane (100 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   Промывкаwashed with water (2×80 mL)
5. 5
   СушкаDichloromethane layer was dried over anhydrous Na2SO4
6. 6
   Другоеevaporated to dryness
7. 7
   ДругоеResidue purified by column
8. 8
   Другоеto get

Методика

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)

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