Acyclic nucleoside analogues from thymine-substituted thymidines and related compounds

Hydrolysis of 3'-deoxy-3'-(thymin-1-yl)thymidine, 3'-deoxy-3'-(uracil-1-yl) thymidine, and related furanoses with two nucleobases has been investigated . 3'-beta-Substituted analogues, but not the 3'-alpha-substituted ones, aff ord isomeric pyranose nucleosides as intermediates, which have been isolate d (6c and 6d). Reduction of the hydrolysis products with sodium borohydride afford the corresponding acyclic compounds (2'-deoxy-D-ribitol or D-ribito l derivatives), which have been fully characterised as their peracetates. ( C) 1999 Elsevier Science Ltd. AII rights reserved.