One-flask syntheses of 6-thioguanosine and 27′-deoxy-6-thioguanosine

Article abstract of DOI:10.1016/0040-4039(91)80589-X

We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.¹ We now report high-yield conversion of guanosine and 2′deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.