Abstract
An antibiotic 2'-amino-2'-deoxyguanosine (I) was synthesized chemically from a guanine 8, 2'-O-cyclonucleoside (II), which could be obtained from guanosine. Compound (II) was converted to N2, 3', 5'-triacetyl derivative (III), which was subjected to opening of the anhydro linkage with liq. H2S in pyridine. Resulting 8-mercaptoarabinofuranosylguanine (IV) was dethiolated and mesylated to give N2, 3', 5'-triacetyl-2'-mesylarabinosylguanine (VI). Deprotection of VI and reprotection with tetrahydropyranyl groups gave compound VIII. Reaction of the compound VIII with sodium azide in acetamide at 210°for 10 min gave 2'-azido compound (IX). The compound IX was deprotected to give 2'-azido-2'-deoxyguanosine (X). Raney nickel catallyzed hydrogenolysis of X gave 2'-amino-2'-deoxyguanosine, which was proved to be identical with a sample of the antibiotic.
