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

The synthesis of two new series of functional phosphines oxides is describe d: analogs of glyphosate (alpha -aminomethylbis(hydroxymethyl)phosphine oxi de] and bisphosphonic acids [bis(hydroxymethyl)phosphoryl methylphosphonic acid] substituting the phosphonic group [-P(O)(OH)(2)] by the bis(hydroxyme thyl)phosphoryl group [-P(O)(CH2OH)(2)], have been synthesized in good yiel ds, using the bis(benzyloxymethyl)chloromethyl phosphine oxide as a common precursor. The further purpose of this work is to evaluate the biological i nterest of the bis(hydroxymethyl)phosphoryl group in comparison to the phos phonic group present in a wide range of biological molecules. (C) 2001 Else vier Science Ltd. All rights reserved.