The excessive hydrophilicity of carbohydrates hampers their application in drug discovery. Deoxyfluorination is one of the strategies to increase sugar lipophilicity. However, lipophilicities of dideoxy-difluorinated monosaccharides are still well below the desired range for oral drug candidates. Here we investigate the power of deoxychlorination to increase sugar lipophilicities. A series of dideoxygenated chloro-fluorosugars was synthesized and for these substrates it was shown that deoxychlorination increased the log  by an average of 1.37 log  units, compared to 0.83 log  units for analogous deoxyfluorination. This shows the potential of deoxychlorination of carbohydrates to increase lipophilicity while limiting the number of potentially important hydrogen bond donating groups to be sacrificed, and will be of interest for glycomimetic development.