Studies on the synthesis and biological activities of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

A series of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by 1H NMR.