Aldophosphamide: synthesis, characterization, and comparison with "Hohorst's aldophosphamide"

Synthesis of aldophosphamide was attempted by many standard aldehyde-forming reactions under a variety of conditions. Trace amounts of aldophosphamide were produced in several of the reactions, as judged by mass-spectral evidence. A stabilized derivative, aldophosphamide semicarbazone, was prepared and characterized by infrared and proton magnetic resonance, and mass spectral analysis) of "Hohorst's aldophosphamide" failed to reveal any evidence for the existence of an aldehyde moiety, and thin-layer chromatographic comparison with the synthetic analogs diethylaldophosphamide and diethylhomoaldophosphamide indicated radical differences in migration rates between those of the analogs and that of "Hohorst's aldophosphamide." It is suggested that "Hohorst's aldophosphamide" is perhaps a diastereoisomer of 4-hydroxycyclophosphamide or an aldehyde hydrate or hemiacetal with 1,3-propanediol.