Synthesis, conformation and antiviral activity of nucleoside analogues with the (2-hydroxy-1-phenylethoxy)methyl glycone—a family of nucleoside analogues related to d4T and aciclovir

Abstract

A complete family of acyclic nucleoside analogues has been obtained by combining the (2-hydroxy-1-phenylethoxy)methyl glycone with the nucleoside bases adenine, guanine, cytosine, thymine and uracil. In each case both optical antipodes have been prepared in enantiomerically pure form from styrene via asymmetric dihydroxylation. The conformation of the uracil and adenine derivatives has been compared by comprehensive calculations using the PM3 method with the conformation of 2′,3′-didehydro-2′,3′-dideoxyuridine (d4U) and the analogous 3-hydroxymethyl-1,3-dihydrobenzo[c]furan nucleoside (bfU). Some antiviral activity has been observed.