NMR spectroscopy and conformational analysis of 3-deoxy-3-C-(hydroxymethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuran ose

Article abstract of DOI:10.1016/0008-6215(93)80004-X

Homonuclear and heteronuclear 1- and 2-dimensional NMR techniques have been used to establish stereochemical and conformational relationships in the hydroxymethyl furanoside 2. Concurrent with the NMR studies, theoretical calculations were performed on this compound using computer-assisted model building (MacroModel) and molecular mechanics (MM2). From the NOE and J-coupling constraints obtained from NMR experiments, refined structures for this compound in two different solvents have been identified and optimized. The 'solvent effects' observed in the NMR spectra for 2 are interpreted in terms of the differences in the requirements for intramolecular electrostatic stabilization in the two solvents. Homonuclear and heteronuclear 1- and 2- dimensional NMR techniques have been used to establish stereochemical and conformational relationships in the hydroxymethyl furanoside 2. Concurrent with the NMR studies, theoretical calculations were performed on this compound using computer-assisted model building (MacroModel) and molecular mechanics (MM2). From the NOE and J-coupling constraints obtained from NMR experiments, refined structures for this compound in two different solvents have been identified and optimized. The ″solvent effects″ observed in the NMR spectra for 2 are interpreted in terms of the differences in the requirements for intramolecular electrostatic stabilization of the two solvents.