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MO-TMS Derivatives of Human Urinary Steroids for GC and GC-MS Studies

1972; Taylor & Francis; Volume: 5; Issue: 1 Linguagem: Inglês

10.1080/00032717208066084

1532-236X

J. P. Thenot, E. C. Horning,

Steroid Chemistry and Biochemistry

Abstract Sterically hindered 17α-hydroxyl groups in steroids are silylated by trimethylsilylimidazole (TSIM) at 100° C. Decreasing rates of reaction were found for the following structures: 17α, 20β, 21-triol > 17α, 20α-diol > 17α, 20α, 21-triol. When methoxime derivatives are formed as the first step, HCL present in the excess of reagent catalyses the silylation reaction of hydroxyl groups. A simple procedure is described whereby methoxime (MO) derivatives are formed in 15 minutes at 60° C (the 11-one group does not react under these conditions) and persilylated compounds are then prepared in 2 hours at 100° C by reaction with trimethylsilylimidazole.