The synthesis of fluorinated carbohydrates and fluorinated cyclohexanols

Abstract

Carbohydrates are central to many fundamental processes. However, their interactions to proteins are characterized by low binding affinity. An attractive strategy to improve this affinity is polyfluorination of carbohydrates. This thesis describes the synthesis and extensive NMR characterisation of monoand difluorinated 2,3-dideoxysugars in which a sugar (CHOH)(CHOH) section was replaced with the more hydrophobic CH2CHF, CH2CF2 and CHFCHF groups. An important consequence of sugar fluorination is that the hydrogen bond properties of the adjacent alcohol group(s) are modified. Part of this thesis describes the synthesis of a number of fluorinated cyclohexanol and benzyl alcohol derivatives as probes to investigate the influence of fluorination on the alcohol hydrogen bond donating capacity