European Journal of Organic Chemistry issue:19 pages:3450-3457
The synthesis and antiviral evaluation of 3'-deoxy-3'-S-phosphonomethyl-3'-thio-alpha-L-threosyl nucleosides as well as the 2'-deoxy analogues related to PMDTT are described. The key transformations involved the synthesis of the 3'-deoxy-3'-thio-L-threosyl and the 2',3'-dideoxy-3'-thio-L-threosyl derivatives by the Mitsunobu reaction. The phosphonate function was introduced by nucleophilic substitution and the glycosylation was carried out under Vorbruggen conditions. None of these synthesized compounds showed significant in vitro activity against HIV, HCV, and RSV, or cytotoxicity.