Synthesis and antiviral activity of the α-analogues of 1,5-anhydrohexitol nucleosides (1,5-anhydro-2,3-dideoxy-D-ribohexitol nucleosides)

Article abstract of DOI:10.1021/jo961982m

1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a ⁴C₁ conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with β-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types 1 and 2.