Synthesis of polyurethanes from saccharide‐derived diols and diisocyanates and their hydrolyzability

Polyurethanes with saccharide moieties in their repeating units (8 and 9) were prepared by polyaddition of methyl α‐ and β‐D‐glucofuranosidurono‐6,3‐lactones (3α and 3β, respectively) and 1,4:3,6‐dianhydro‐D‐glucitol (4) with hexamethylene diisocyanate (5a) and methyl (S)‐2,6‐diisocyanatohexanoate (5b), which was derived from L‐lysine, in N,N‐dimethylformamide at 25°C using dibutyltin dilaurate as a catalyst. Their properties were compared with those of the polyurethanes (6 and 7) prepared from D‐glucaro‐1,4:6,3‐dilactone (1) and D‐mannaro‐1,4:6,3‐dilactone (2), respectively, in our previous work. Hydrolyzability of the polyurethanes containing 1, 2, or 3α units in buffer solutions was found to be higher than that of the polyurethanes derived from 3β or 4.