Thermodynamic stabilities and conformational analyses of 4,6- O-acetalized 1,5-anhydro-5-thio- dl- threo-2-enitols

• Published in: Carbohydrate research Vol. 344; no. 7; pp. 928 - 932
• Main Authors: Watanabe, Yuhya, Sakakibara, Tohru
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 12.05.2009; Elsevier
• Subjects: 4,6- O-Neopentylidene acetal; 5-Thiosugar; Biochemistry & Molecular Biology; Carbohydrate Conformation; Chemistry; Chemistry, Applied; Chemistry, Organic; Conformation; Drug Stability; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; Physical Sciences; Science & Technology; Sugar Alcohols - chemistry; Thermodynamic stability; 5-Thiosugar; Thermodynamic stability; 4,6- O-Neopentylidene acetal; Conformation; 4,6-O-Neopentylidene acetal
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2009.02.028

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.