Chloride → 3′-Azido-3′-deoxyadenosine

Participants

Reaction Steps

3′-Azido-3′-deoxyadenosine is synthesized as described by Robins et al. (J. Org. Chem. 66:8204-8210, 2001). 3′-azido-3′-deoxyguanosine (2.92 g; 10 mmol) is dissolved in anhydrous pyridine (60 mL) with vigorous stirring under an argon atmosphere and cooled on an ice bath, followed by treatment with trimethylsylil chloride (3 molar equivalents; mol eq), and stirring for 60 minutes at room temperature. The resulting solution containing the sylilated nucleoside is cooled on an ice bath and treated with benzoyl chloride (1.2 mol eq), allowed to reach room temperature, and then stirred for 4 hours. Water (10 mL) is added and the solution is stirred for 10 minutes. Concentrated ammonium hydroxide (20 mL) is added and the reaction mixture is stirred for 15 minutes at room temperature. The resulting mixture was then evaporated to dryness under reduced pressure. The dried residue is stirred with cold water, filtered, and dried under high vacuum with phosphorus pentoxide, yielding 3′-azido-6-N-benzoyl 3′-deoxyadenosine.

Provenance & Evidence