In this study, tailored polyurethanes with possible biological, biomedical, and/or pharmacological uses are synthesized and carefully characterized. Poly(-caprolactone) diol was used as the diol, 1,6-hexamethylene diisocyanates as the aliphatic diisocyanate, tin (II) 2-ethylhexanoate as the catalyst, glucose as the chain extender/crosslinking agent to create polyurethanes, and dimethyl sulfoxide as the solvent in combination with glucose to create several polyurethane samples. Additionally, there were order-of-magnitude variations in the mol ratios of the glucose. The five-hydroxyl group of glucose was discovered to have variable reactivity, and swelling studies carried out in a variety of solvents with varied polarity showed that dimethyl-sulfoxide exhibited the greatest degree of swelling. The crosslink densities were calculated from the data of the swelling experiments.