Synthesis and structure of S-nucleosidyl S-aryl disulfides and their reaction with phosphites

Article abstract of DOI:10.1016/0040-4020(95)00936-1

A general procedure for the preparation of S-nucleosidyl S-aryl disulfides from the corresponding thioesters is described. This procedure has been used for the preparation of a ribonucleoside disulphide (8d), a key intermediate for the synthesis of oligoribonucleotides containing 3'-S-phosphorothiolate linkages. The regioselectivity of the Arbusov reaction of 8d with phosphites has been examined. The X-ray structure of 3'-deoxy-3'-S-(2-nitrophenyldisulfanyl)thymidine (9b) is also reported.