RESEARCH ARTICLE

 

Study of cyclization of diphenylacetals derived from L-rhamnose and L-fucose: A theoretical approach

 

 

A.E. Bañueios-Hernández^I; J.A. Mendoza-Espinoza^{II, *}

^IDepartamento de Farmacología, Centro de Investigación y de Estudios Avanzaados del Instituto Politécnico National, México D.F
^IILaboratório de Productos Naturales. Academia de Biología Humana, Colegio de Ciencia y Tecnología, Universidad Autónoma de la Ciudad de México, México D.F

 

 

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ABSTRACT

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 AM₁ 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.

Keywords: Molecular modelling, conformational analysis, Monte Carlo conformational search method, L-rhamnose, L-fucose, B3LYP, DGDZVP, diphenylthioacetal

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Received 18 October 2011
Revised 20 February 2012
Accepted 22 March 2012

 

 

*To whom correspondence should be be addressed. E-mail: amendozaespinoza@gmail.com / josealberto.mendoza@uacm.edu.mx