HCID 86583743, compound → (2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylic acid

Participants

Reaction Steps

A solution of 1.72 g (3.85 mmol) of (2S,1 R,4R,5R)-4-(6-amino-2-iodopurin-9-yl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]octane-2-carboxylic acid (6.7) in 80 mL of 50% HCOOH was stirred at 80° C. for 1.5 hours. The reaction mixture was evaporated under reduced pressure, dissolved in H2O, and the solution was evaporated again. This process was repeated until there was no odor of formic acid in the residue. Recrystallization from water yielded 1.33 g (85%) 6.8 as a white solid, m.p. 221-223° C. dec. 1H NMR (300 MHz, DMSO-d6) δ8.31 (s, 1H, H-8), 7.68 (s, 2H, NH2), 5.90 (d, J=6.55 Hz, 1H, H-1′), 4.42 (m, 1H, H-2′), 4.35 (d, J=2.31 Hz, 1H, H-4′), 4.22 (m, 1H, H-3′).

Provenance & Evidence