Fluorinated sugars are widely studied as inhibitors and transporters in biological systems. The perfluorinated α-D-pentofuranoses were modeled computationally with B3LYP/6-311G(d,p) and plotted utilizing the Rhoad-Cagg-Carver method. The computations indicate that the conformational preferences of the perfluorinated sugars with respect to the fluoro-methyl group are gt, with the preferential ring conformation varying greatly with stereochemistry. The desired pertosylated intermediate of arabinose, lyxose, and xylose, that were synthesized using toluenesulfonyl chloride in pyridine, have been confirmed using proton NMR spectroscopy and are currently being isolated and categorized. The next stage of the project will be to develop the synthesis of the perfluorinated α-furanoses from the pertosylated intermediates.

Energies and conformational preferences of perfluorinated α-furanoses

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.