A dideoxydidehydronucleoside derivative

Abstract

We have synthesized a di­deoxy­dide­hydro­nucleoside derivative, 2(S)-acetoxymethyl-4-[4-amino-2-oxopyrimidin-1(2H)-yl]-2,5-di­hydro­furan, C11H13N3O4, which is an analogue of the potently anti-HIV active compound, di­deoxy-dide­hydro­cytidine (d4C). The target compound crystallizes with two mol­ecules in the asymmetric unit that differ primarily in the orientation of the C6′-acetyl group. One mol­ecule has an extended conformation and the orientation of the acetyl group in the second mol­ecule gives an unusual hooked-shaped conformation. The two conformers form A–B dimers via N—H⋯N hydrogen bonds. The dimers link via N—H⋯O hydrogen bonds to form chains parallel to the b cell axis.