Synthesis and stereochemistry of 6-membered ring phosphonates

Abstract

Abstract Background: Organophosphorus compounds have important industrial and biomedical applications as pharmaceutical and agrochemical agents, as well as transition state analogs for the production of monoclonal antibodies. Methods: Two diastereomers of a 6-membered ring, cyclic phenyl phosphonate were synthesized in 8 steps from 1,3-butanediol. Results: The stereochemistry of the diastereomers was elucidated on the basis of 3 1 P NMR signals, together with 1 H NMR nuclear Overhauser effects (NOE) difference experiments. Conclusions: Such cyclic phosphonates may have utility serving as transition state analogs for the production of monoclonal antibodies.