Ethyl Acetate → HCID 178430608, compound

Participants

Reaction Steps

To a solution of 3'-(t-butyldimethylsilyl)thymidine (1.10 g, 3.09 mmol) and diisopropylehtylamine (1.40 mL, 6.18 mmol) in anhydrous methylene chloride at 0° C. under argon was added dropwise 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (2.15 mL, 12.36 mmol). The resulting solution was stirred at room temperature for 30 min, diluted at 0° C. with ethyl acetate, washed with cold 5% sodium bicarbonate twice, dried over sodium sulfate, and concentrated to dryness at 25° C. Chromatography on silica gel with triethylamine-ethyl acetate-hexanes (5:40:55) gave 1.25 g of the titled compound as a colorless foam, which contained two diastereomers (ratio ~1:1).

Provenance & Evidence