Acyclic Analogs of Nucleosides. Synthesis of Chiral 1,5-Dihydroxy-4-methyl-3-oxapent-2-yl Derivatives of Uracil

Article abstract of DOI:10.1007/BF00475574

A convenient method has been developed for the synthesis of optically active 1-<1,5-dihydroxy-4-(R)-methyl-3-oxapent-2(R and S)-yl>uracils. 5'-Deoxyuridine is obtained from 2',3'-O-isopropylideneuridine, and its periodate oxidation followed by reduction with sodium tetrahydroborate leads to the desired 4(R),2(R)-isomer.The acetonide of α-uridine is converted into the 4(R),2(S)-isomer analogously.