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Cbz-aminomethylphosphonic acid as well as its P=S, P=Se and P-BH3 analogs were synthesized using DMSO/I2 and a three-step, one-pot procedure respectively. In all cases the corresponding Cbz-aminomethylphosphinic acid was the starting material. The latter case, oxidation of the BSA-generated disilylester using elemental sulfur, selenium and BH3.Me2S followed by methanolysis represents a convenient, high yielding synthetic method for these useful building blocks. The stability of the compounds under several conditions is also discussed.

Cbz-aminomethylphosphonic acid and its structural variations: synthesis from a common precursor and a stability study