The development of transformation routes that efficiently convert biomass-derived intermediates into products that are compatible with the existing fuel infrastructure, which fit within the specifications for gasoline, jet and diesel fuels, is currently an area of intense research interest. The potential routes for decreasing the oxygen content of biomass intermediates include decarboxylation, dehydration, and hydrodeoxygenation. Rejection of oxygen as carbon dioxide, decarboxylation, results in significant carbon and mass loss from sugars, while rejection of oxygen as water, dehydration, leads to unsaturated products and undesirable tars. Hydrodeoxygenation, using hydrogen to remove oxygen as water, produces saturated products and retains carbon, however, uses expensive hydrogen, catalysts and often severe conditions. This presentation will discuss the difficulties in converting sugars to hydrocarbons and compare the different routes using practical examples to highlight the impact of choosing one route over another.