Mc. Trinh et al., SYNTHESIS AND ANTIVIRAL STUDY OF ACYCLIC ANALOGS OF 3'-AZIDO, 3'-AMINO, AND 3'-FLUORO-3'-DEOXYTHYMIDINE, AND OF HEPT ANALOGS, Synthesis, (9), 1994, pp. 939-943
Several new acyclonucleosides have been synthesized from racemic epich
lorhydrin or epifluorhydrin. This involves epoxide opening followed by
chain elongation with iodomethyl phenyl sulfide and subsequent coupli
ng of the phenylthioacetal with thymine. Deprotection afforded the tit
le compounds 6, 8 and 18, whereas introduction of a phenylthio group a
t C-6 led to the three HEFT analogs, 13, 19, and 24.