Self-Polyaddition of Six-Membered Cyclic Carbonate Having Fmoc-Protected Amino Group:  Novel Synthetic Method of Polyhydroxyurethane

This article deals with the self-polyaddition of 3-(1,3-dioxan-2-one-5-yl)propyl 2-(9-fluorenylmethoxycarbonylamino)ethyl thioether by the deprotection of the 9-fluorenylmethyoxycarbonyl (Fmoc) group with N, N -diisopropylethylamine, 4-(dimethylamino)pyridine, or triethylamine as a novel synthetic method of a polyhydroxyurethane. The polymer with higher yields and M n 's was obtained by using N, N -diisopropylethylamine and 4-(dimethylamino)pyridine than triethylamine. Fmoc deprotection and stability of the cyclic carbonate group were elucidated to optimize the condition by using the model compounds, 3-cyclohexylpropyl 2-(9-fluorenylmethoxycarbonylamino)ethyl thioether and 3-(1,3-dioxan-2-one-5-yl)propyl ethyl thioether.