Stereochemical effects in fragmentation of diastereoisomers of protected diethyl 1,2-diamino-alkylphosphonates

Rapid Communications in Mass Spectrometry : RCM
Ewelina DrabikMarek Sochacki

Abstract

Diastereoisomers of diethyl 5-substituted (2-thioxo-imidazolidin-4-yl)phosphonates, which can be regarded as protected diethyl 1,2-diaminoalkylphosphonates, have been analyzed by electron ionization mass spectrometry. Significant differences in the fragmentation of cis- and trans-diastereoisomers were found. The stereospecificity of the elimination of diethyl phosphonate and the loss of the diethoxyphosphoryl group were studied using specific labeled compounds and collision-induced dissociation. The relative abundances of ions formed via these fragmentation processes can be used for differentiation of both diastereoisomers.

References

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Jan 31, 2007·Rapid Communications in Mass Spectrometry : RCM·G S RamanjaneyuluG Narahari Sastry
Aug 15, 2009·Rapid Communications in Mass Spectrometry : RCM·B RajuR Srinivas

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Citations

Feb 9, 2013·Journal of the American Society for Mass Spectrometry·Ewelina DrabikMarek Sochacki
Jul 11, 2012·Rapid Communications in Mass Spectrometry : RCM·Donghui BaoMichael J Sofia
Mar 19, 2011·Rapid Communications in Mass Spectrometry : RCM·Gaurao D TibheMario Ordóñez
Feb 22, 2011·Rapid Communications in Mass Spectrometry : RCM·Basem KanawatiPhilippe Schmitt-Kopplin

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