Lithium hydride as an efficient reagent for the preparation of 1,2-anhydro inositols: Does the reaction proceed through 'axial rich' conformation?
Carbohydr Res
; 463: 32-36, 2018 Jun 30.
Article
em En
| MEDLINE
| ID: mdl-29751207
ABSTRACT
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.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos de Epóxi
/
Inositol
/
Lítio
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article