Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester → (2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-iodo-9H-purin-9-yl)tetrahydro-3-furanyl acetate (J. Med. Chem., 1992, 35, 248) (0.5 g, 0.93 mmol) and copper (II) cyanide (0.11 g, 1.23 mmol) in N,N-dimethylformamide was heated at 115° C. for 90 minutes. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1 by volume) to give a product which was then azeotroped sequentially with dichloromethane and diethyl ether to afford the title compound as a solid (0.22 g).

Provenance & Evidence