Organic & Biomolecular Chemistry

Abstract

Michaelis – Arbuzov reactions of S -aryl disul fi de derivatives of 3 ’ -thiothymidine or 5 ’ -thioadenosine with tris(trimethylsilyl) phosphite proceeded in high yields to the corresponding phosphorothiolate monoesters. Subsequent hydrolytic desilylation and phosphate coupling were e ff ected in one-pot using liquid-assisted grinding in a vibration ball mill. Novel 3 ’ ,5 ’ - and 5 ’ ,5 ’ -pyrophos-phorothiolate-linked dinucleoside cap analogues were thereby prepared.