Triphenylphosphine → HCID 87593598, compound

Participants

Reaction Conditions

Reaction Steps

370 mg (1.0 mmol) (1R,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-[(tert-butyldimethylsilyloxy)methyl]-2-methylene-cyclopentanol (Compound 4a, R1═R2=t-BuMe2Si), 338 mg (2.0 mmol) 6-chloro-2-aminopurine (Compound 23) and 524 mg Ph3P (2.0 mmol) were placed into 20 ml round bottom flask, to which 5 ml anhydrous THF was then added. The mixture was cooled to −23° C., to which a solution of 350 mg DEAD (1.0 mmol)/5 ml THF was added dropwise. After addition was completed, the reaction mixture was stirred at −23° C. for 3.5 hours, warmed to room temperature and stirred at room temperature overnight. Subsequently THF was evaporated off under reduced pressure. 10 ml t-BuOMe was added to the residue. The mixture was stirred for 5 minutes, to which 15 ml n-hexane was added. The mixture was maintained standing for 5 hours, and filtered to remove insoluble substance. The filtrate was purified with column chromatography, eluting with petroleum ether/EtOAc (3/1 (v/v)), to afford 305 mg (59%) of title compound as light yellow oil.

Provenance & Evidence