Synthesis of bis(2-chloroethyl)amides of polyhydroxy acids

The bis(2-chloroethyl)amides of peracetylated L-arabonic, D-gluconic, and D-galactaric acids were synthesized. The acetyl protection in the obtained compounds is removed anomalously in alkaline media (ammonia, triethylamine, barium methoxide), but in acidic media (HCl) complete deacetylation occurs with the formation of the bis(2-chloroethyl)amides of the respective acids. The PMR spectra were obtained on a Tesla BS-497 spectrometer at 100 MHz in deuterochloroform with HMDS as internal standard. The chemical shifts are given with reference to TMS. The 13C NMR spectra were recorded on a Bruker WM-250 instrument at 62.89 MHz in deuterochloroform or heavy water with methanol as standard