Stadler, G. (2021). Synthesis and characterization of 17-epistanozolol- N-glucuronides for anti-doping purposes [Diploma Thesis, Technische Universität Wien]. reposiTUm. https://doi.org/10.34726/hss.2021.86891
The aim of this thesis was the synthesis of urinary metabolites of the anabolic androgenic steroid stanozolol for anti-doping purposes and comparison with human metabolic molecules. Focus was put on the synthesis of the in position 17 epimerized metabolite of stanozolol and the N glucuronides of this molecule. Synthesis of 17-epistanozolol was carried out starting from stanozolol via sulfation of the tertiary alcohol and hydrolysis under basic conditions. N Glucuronides of this product were synthesized through modified Koenigs-Knorr glycosylation conditions with mercury salts for activation. The obtained synthetic metabolites were deprotected under basic conditions, fully characterized and compared with human urinary metabolic products.
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