Reacción #51521

Ecuación de reacción

triethylamine

t-butyldiphenylsilyl chloride

3′-O-allyl-N6-benzoyl adenosine

P2O5

→

title compound

Rendimiento 49.0%

3′-O-allyl-5′-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine

Rendimiento 49.0%

Disolventes

CH2Cl2

ethyl acetate hexane

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroReaction
2. 2
   Lavadowashed with water (3×30 mL)
3. 3
   SecadoDichloromethane layer was dried over anhydrous Na2SO4
4. 4
   Otroevaporated to dryness
5. 5
   OtroResidue purified by flash chromatography (ethyl acetate:hexane 1:1 as eluent)

Procedimiento

2′/3′-O-allyl-N6-benzoyl adenosine (11.17 g, 27.84 mmol) was dried over P2O5 under vacuum at 40° C., then dissolved in dry CH2Cl2 (56 mL, sure seal from Aldrich). 4-dimethylaminopyridine (0.34 g, 2.8 mmol), triethylamine (23.82 mL, 167 mmol) and t-butyldiphenylsilyl chloride were added. The reaction mixture was stirred vigorously for 12 hr. Reaction was monitored by TLC (ethyl acetate:hexane 1:1). It was then diluted with CH2Cl2 (50 mL) and washed with water (3×30 mL). Dichloromethane layer was dried over anhydrous Na2SO4 and evaporated to dryness. Residue purified by flash chromatography (ethyl acetate:hexane 1:1 as eluent) to get the title compound as a white foam (8.85 g, 49%). Rf 0.35 (ethyl acetate:hexane, 1:1)

Fuente