An acyclonucleoside synthesis was investigated on the regioselective i
ntroduction of an acyclochain. We found that iodotrimethylsilane catal
yzed the reaction of acyclochain introduction as well as its migration
from S-2 to N-1 of 2-thiothymine and from N-7 to N-9 position of guan
ine. By taking the findings into account, several acyclonucleosides we
re synthesized in a simple one-pot procedure.