title: Thermodynamic stabilities and conformational analyses of 4,6-O-acetalized 1,5-anhydro-5-thio-DL-threo-2-enitols.
abstract: 4,6-O-Methylidene and 4,6-O-neopentylidene derivatives of 1,5-anhydro-2,3-dideoxy-5-thio-DL-thero-hex-2-enitol having the C-inside form were found to be thermodynamically more stable than the corresponding O-inside conformers. Thermodynamic stabilities, as well as the conformation of sulfoxide and sulfone derivatives of the 4,6-O-neopentylidene compound were examined by experiment and ab initio MO and DFT calculations. These thermodynamic stabilities, and the most stable conformations determined by NMR data, were corroborated by calculations.
authors.affiliation: Graduate School of Integrated Science, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan.
authors.forename: Yuhya
authors.initials: Y
authors.lastname: Watanabe
authors.forename: Tohru
authors.initials: T
authors.lastname: Sakakibara