The crystal structure of ethyl 2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside. 1984

L M Wingert, and J R Ruble, and G A Jeffrey

The crystal structure of ethyl 2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside, C8H14O4, is orthorhombic, P2(1)2(1)2(1), with cell dimensions at 123 K [293 K] a = 11.220(2) [11.319(1)], b = 18.387(3) [18.458(2)], c = 8.509(2) [8.635(1)] A, Z = 8. There are two symmetry-independent molecules in the asymmetric unit. In both molecules, the conformation is oH5. The alkenic bond is almost exactly planar in one molecule, with C-1--C-2--C-3--C-4 = +0.8 degrees. In the other molecule, this torsion angle is +3.7 degrees. The glycosidic torsion angle, O-5--C-1--O-1--C-7, has normal exoanomeric values of +71 and +64 degrees. The conformation of the ethoxyl group is extended, with C-1--O-1--C-7--C-8 = +162 and +170 degrees. The primary alcohol group has different orientations, g/t on one molecule, g/g on the other. The characteristic glycosidic bond-shortening observed in the pyranosides is modified in this enopyranoside. Both the ring bond, O-5--C-1, and the glycosidic bond, C-1--O-1, are short, with distances ranging from 1.409 to 1.425 A. Solution and solid-state c.p.-m.a.s., 13C-n.m.r. spectra are reported.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D006601 Hexoses MONOSACCHARIDES whose molecules contain six carbon atoms, such as GLUCOSE and FRUCTOSE. They generally have the chemical formula C6H12O6. Hexose
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond

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