Structure of 2-C-(hydroxymethyl)-d-ribose (hamamelose) in the solid-state analyzed by CP MAS NMR and X-ray crystallography Original Research Article

d-Hamamelose, a branched-chain ribose (2-C-(hydroxymethyl)-d-ribose), has been synthesized and its solid-state structure analyzed by 13C CP MAS NMR spectra and X-ray data. The presence of the complex pattern of resonances in the anomeric region, as well as in the ring carbon region, in 13C CP MAS NMR spectrum indicated that the mixture of four cyclic forms, α- and β-furanoses, as well as both α- and β-pyranoses were present in the solid-state. X-ray analysis of crystals showed that d-hamamelose belongs to the monoclinic system with unit cell: a = 4.790 Å, b = 8.671 Å, c = 8.880 Å and β = 98.89°, space group P21. The furanose ring has the 2E conformation.