Summary.
O-Cholesteryl-O-phenyl-N-phenylphosphoramidate was synthesized as intermediate for the stereoselective synthesis of organophosphates and phosphorothioates. Single crystal X-ray diffraction discerned four independent P-epimeric phosphoramidates cocrystallizing in the triclinic P1 space group. They were found to be selectively paired in the crystal forming pseudo-centrosymmetric dimers via hydrogen bonds between the amide group of one epimer and the phosphinoyl group of the other.
Zusammenfassung.
O-Cholesteryl-O-phenyl-N-phosphoramidat wurde als Zwischenprodukt für die stereoselektive Synthese von Organophosphaten und Phosphorthioaten dargestellt. Die Einkristallröntgenstrukturanalyse ergab vier unabhängige P-epimere Phosphoramidate, die in der triklinen Raumgruppe P1 kristrallisieren. Sie liegen im Kristall selektiv gepaart in From von pseudo-zentrosymmetrischen Dimeren vor, die über Wasserstoffbrücken zwischen der Amidgruppe des einen Epimers und der Phosphinoylgruppe des zweiten aneinander gebunden sind.
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Received December 11, 1998. Accepted (revised) February 17, 1999
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Cea-Olivares, R., López-Cardoso, M. & Toscano, R. Synthesis and Structural Characterizationof the Two Epimeric O-Cholesteryl-O-phenyl-N-phenylphosphoramidates. Monatshefte fuer Chemie 130, 1129–1136 (1999). https://doi.org/10.1007/PL00010291
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DOI: https://doi.org/10.1007/PL00010291