TY - JOUR T1 - Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: does the reaction proceed through 'axial rich' conformation? JF - Carbohydrate Research Y1 - 2018 A1 - Sarkar, Nitai A1 - Sardessai, Richa S. A1 - Shashidhar, Mysore S. A1 - Tamboli, Majid I. A1 - Gonnade, Rajesh G. AB - scyllo-Inositol derived 1,2-trans-diequatorial halohydrins can be efficiently converted to the corresponding epoxides in the presence of lithium hydride. The structure of one of the epoxides was determined by single crystal X-ray diffraction analysis. This provides a potential route for the preparation of ring modified inositol derivatives. DFT calculations suggest that this epoxide formation could be proceeding through the intermediacy of the cyclohexane ring-inverted axial-rich conformer (1,2-trans-diaxial halohydrin). This is supported by the results of DFT calculations on the formation of inositol orthoformate, where the product is locked in the axial-rich conformation, while the starting inositol has the equatorial-rich conformation. VL - 463 U3 - Foreign U4 - 2.096 ER -