Diiodomethane → Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Participants

Reaction Steps

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(2-amino-6-chloropurin-9-yl)oxolan-3-yl acetate (3.8 g, 8.88 mmoles) in acetonitrile (40 ml) was added diiodomethane (3.4 ml) and n-amyl nitrite (8.2 ml). The resulting mixture was refluxed overnight, then the solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with a mixture of 40% ethanol/60% hexane, to provide (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate (2.7 g) as a light yellow solid.

Provenance & Evidence