Synthesis of bis(hydroxymethyl)phosphorylated compounds, analogs of α-aminophosphonic acids or alkylidenebisphosphonic acids

The synthesis of two new series of functional phosphines oxides is described: analogs of glyphosate [α-aminomethylbis(hydroxymethyl)phosphine oxide] and bisphosphonic acids [bis(hydroxymethyl)phosphoryl methylphosphonic acid] substituting the phosphonic group [–P(O)(OH)2] by the bis(hydroxymethyl)phosphoryl group [–P(O)(CH2OH)2], have been synthesized in good yields, using the bis(benzyloxymethyl)chloromethyl phosphine oxide as a common precursor. The further purpose of this work is to evaluate the biological interest of the bis(hydroxymethyl)phosphoryl group in comparison to the phosphonic group present in a wide range of biological molecules.