Synthesis of 3α,6β‐Dihydroxyandrostan‐17‐one 3‐Glucuronides for the Detection of Testosterone Misuse

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The effortless synthesis of two 3-glucuronide conjugates of 6β-hydroxyandrosterone (6OH-And-3G 2 ) and 6β-hydroxyetiocholanolone (6OH-Etio-3G 3 ) is reported. The conjugates are determined as long-term markers of endogenous androgenic anabolic steroid abuse in doping regulate scientific tests. Their resistance to enzymatic hydrolysis by E. coli β-glucuronidase suggests they may possibly be skipped by standard GC-MS evaluation protocols. One promising strategy to quantify these markers is by direct procedures, which necessitates ample portions of large purity reference components. Our convergent synthesis features concurrent stereoselective introduction of 5α/5β hydrogen and 6β-hydroxy teams on the steroid skeleton, and a mild Schmidt trichloroacetimidate glycosylation strategy.

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