oa South African Journal of Chemistry - Study of cyclization of diphenylacetals derived from L-rhamnose and L-fucose : a theoretical approach : research article
|Article Title||Study of cyclization of diphenylacetals derived from L-rhamnose and L-fucose : a theoretical approach : research article|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Affiliations||1 Centro de Investigacion y de Estudios Avanzados del Instituto Politecnico Nacional, Mexico and 2 Universidad Autonoma de la Ciudad de Mexico, Mexico|
|Publication Date||Jan 2012|
|Pages||84 - 90|
|Keyword(s)||B3LYP, Conformational analysis, DGDZVP, Diphenylthioacetal, L-fucose, L-rhamnose, Molecular modelling and Monte Carlo conformational search method|
This work aimed to study the configuration of two mono-tosyl-diphenylacetals, highly flexible molecules derived from L-ramnose and L-fucose, by means of the Monte Carlo conformational search method. The energy of the conformers established by this method and calculated by using the molecular mechanics force field (MMFF) permitted to establish a first conformational space. The geometry of the conformers was optimized by using the semi-empirical AM and the density functional B3LYP/DGDZVP methods. We were able to explain the different final products recovered from the reaction of the diphenylacetals derived from L-rhamnose and L-fucose with tosyl chloride, in a pyridine solution. On the other hand, obtaining cyclical compounds by intramolecular cyclization could be an attractive pathway for the synthesis of furanosides.
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