A promising trend in the search for new more effective and selective drugs is the search for structural analogues of amino acids. The structures and activities of both enanti­omeric diethyl (1S,2R)- and (1R,2S)-1,2-bis­(tert-but­oxy­carbonyl­amino)­propyl­phospho­nates (as the monohydrates, C17H35N2O7P·H2O), 1 and 2, respectively, and racemic diethyl (RS)-2-(tert-but­oxy­carbonyl­amino)­propyl­phospho­nate, 3, have been determined. The anti­microbial activity of 1, 2 and 3 was tested against reference bacterial strains and showed weak bioactivity against Gram-positive bacteria. ADME (absorption, distribution, metabolism and excretion) analysis indicates that the com­pounds may have gastrointestinal absorption. The compounds satisfy Lipinski's rules. Keywords: propylphos­pho­nate derivatives; anti­bacterial activity; enanti­omer; racemate; crystal structure; pharmacokinetics