SYNTHESIS OF 2'-SUBSTITUTED SULFIDE-LINKED DINUCLEOTIDES

Abstract 3′-Deoxy-3′-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2′-methoxy (16) and 2′-deoxy (38) analogs were condensed with 5′-deoxy-5′-thiothymidine 4 and 17 or 2′-O-methyl-5′-deoxy-5′-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.