Diastereoselective synthesis of the major products resulting from the interaction between ionizing radiation and thymidine

5,6-Dihydro-5,6-dihydroxythymidine (thymidine glycol, 1) and 5,6-dihydro-5-hydroxy-thymidine (C5-thymidine hydrate, 2) are the major products attributed to the effects of γ-radiolysis on thymidine under aerobic and hypoxic conditions, respectively. The authors have achieved the first chemical synthesis of 2 from the respective cis-glycols. Diastereoselective synthesis of 1 and 2 is achieved by carrying out a stereoselective dihydroxylation on the bis-t-butyl-dimethylsilyl ether of thymidine