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  • Title: Thermodynamic stabilities and conformational analyses of 4,6-O-acetalized 1,5-anhydro-5-thio-DL-threo-2-enitols.
    Author: Watanabe Y, Sakakibara T.
    Journal: Carbohydr Res; 2009 May 12; 344(7):928-32. PubMed ID: 19327754.
    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.
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