Conformational and reactivity study of dithiophenyl-fucosyl ketals with theoretical chemical methods
Angel E Bañuelos-Hernandez1, Hugo A García-Gutiérrez2, Mabel Fragoso-Serrano3
1Programa de Posgrado en Farmacología, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Mexico, Mexico.
Abstract:
Carbohydrates can be used as substrates to synthesize new complex molecules; these molecules contain several chiral centers that can be used in organic synthesis. D-Fucose diphenyl thioacetal reacts differentially with acetone, and this paper describes a study of the mechanism of this reaction using theoretical chemistry methods. The conformer distribution was studied using a Monte Carlo method for the reaction products, and the obtained conformers were validated by calculating the hydrogen spin-spin coupling constants with the DFT/B3LYP/DGDZVP method. Results agreed with the experimental coupling constants with an adequate root mean squared deviation. The free energies and enthalpies of formation of the resulting global minimum conformers were calculated with the same method and with the thermochemical compound method CBS-4 M. This technique, combined with the conformational analysis, allowed comparison of the formation enthalpies of the compounds involved in this reaction, and, with this information, we can postulate the correct reaction pathway. Graphical abstract Reaction pathway.
More Related Videos
07:07Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
UV–Vis Spectroscopy: Woodward–Fieser Rules
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Preparation and Reactions of Sulfides
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
