An intramolecular benzyl rearrangement of 1-(N-benzyloxycarbonylamino)alkylphosphonate diesters under electrospray ionization conditions.
The mass spectrometric behavior of eleven 1-(N-benzyloxycarbonyl(Cbz)amino)alkylphosphonate diesters was studied under positive ion electrospray ionization (ESI) conditions. Their fragmentation pathways are depicted and supported by tandem mass spectrometry. Besides the common eliminations of ether, benzyl alcohol, phosphite and an ether plus benzyl alcohol from molecular ions, the title compounds show a tendency to undergo an interesting intramolecular benzyl rearrangement to yield benzylphosphonate ions. The fragmentation patterns do not depend on the substituent attached to the alpha-carbon atom.
Ma
Yuan
Y
The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Science and Engineering, Tsinghua University, Beijing 100084, China. mayuan@mail.tsinghua.edu.cn
Chen
Yi
Y
Sun
Ming
M
Zhao
Yufen
Y
D004791:Enzyme Inhibitors / Q000032:analysis / Q000737:chemistry; D004952:Esters / Q000032:analysis / Q000737:chemistry*; D019606:Phosphoamino Acids / Q000032:analysis / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D004791:Enzyme Inhibitors; D004952:Esters; D019606:Phosphoamino Acids