Triethylamine → 3'-O-allyl-5'-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine

Participants

Reaction Steps

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)

Provenance & Evidence