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.
Original language | English |
---|---|
Pages (from-to) | 84-90 |
Number of pages | 7 |
Journal | South African Journal of Chemistry |
Volume | 65 |
State | Published - 2012 |
Externally published | Yes |
Keywords
- B3LYP
- Conformational analysis
- DGDZVP
- Diphenylthioacetal
- L-fucose
- L-rhamnose
- Molecular modelling
- Monte Carlo conformational search method