The first structurally analysed nucleic acid building block containing the Reese protecting group: 2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-β-D-(1'R,2'R,3'R,4'R)-uridine.

Abstract

The title compound, C21H26FN3O7, is assembled by N-H...O and O-H...O hydrogen bonds into well-separated two-dimensional layers of about 15 Å thickness. The crescent conformation of the molecules is stabilized by weak intramolecular C-H...O and C-H...F hydrogen bonds. The uridine moiety adopts an anti conformation. The ribofuranose ring exists in an envelope conformation. All the endocyclic uracil bonds are shorter than normal single C-N and C-C bonds, and five of them have comparable lengths, which implies a considerable degree of delocalization of the electron density within this ring.