Action of nucleophiles on 2,3'-anhydrothymidine: Side-reactions involving the possible intermediacy of 2,5'-anhydro-1-(2-deoxy-β-D-threo-pentofuranosyl)thymine

Article abstract of DOI:10.1016/S0040-4039(00)74215-8

2,3'-Anhydrothymidine (1) reacts with the sodium salt of propane-2-thiol and with sodium phenyl selenide to give 5'-substituted products [(3b) and (3c), respectively] in addition to the expected 3'-substituted 2',3'-dideoxynucleoside derivatives [(2b) and