A facile and high yielding synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide--an internal standard in dope |
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| Authors: | Gärtner Peter Novak Clemens Einzinger Christian Felzmann Wolfgang Knollmüller Max Gmeiner Günter Schänzer Wilhelm |
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| Affiliation: | Institute of Organic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria. pgaertner@mail.zserv.tuwien.ac.at |
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| Abstract: | A facile six-step synthesis of 2,2,3,4,4-d5-androsterone-beta-D-glucuronide (1) starting from epiandrosterone (2) in 63% yield is described and compared with several alternative synthetic pathways. Compound 1 can be used as an internal standard in screening procedures for anabolic steroids to monitor the hydrolysis step of the steroid glucuronides prior to gas chromatography-mass spectrometry (GC-MS) analysis. Thus, a time consuming solid-phase extraction step to remove possible hydrolysis inhibitors can be omitted. |
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| Keywords: | Androgen glucuronide Deuterium addition Diastereoselective reduction Doping control Stereoselective synthesis Steroid |
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