title: First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis.
abstract: The first synthesis of 16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol (8) in 26% yield over nine steps is described using moderately priced starting materials and economic amounts of reagents. Compound 8 can be used as an internal standard in screening procedures for anabolic steroids as well as for the quantification of stanozolol metabolites via mass spectrometric techniques, such as LC-MS or gas chromatography-mass spectrometry (GC-MS).
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Felzmann
authors.forename: Günter
authors.initials: G
authors.lastname: Gmeiner
authors.forename: Peter
authors.initials: P
authors.lastname: Gärtner
mesh_terms: D000738:Androsterone / Q000138:chemical synthesis* / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D008968:Molecular Conformation; D012015:Reference Standards; D013197:Stanozolol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000592:standards
chemical_list: C501386:16,16,20,20,20-pentadeuterio-3'-hydroxystanozolol; D013197:Stanozolol; D000738:Androsterone