94977-66-9Relevant academic research and scientific papers
18-Substituted Steroids. Part 11. Synthesis of 3&β,16&α,18-Trihydroxyandrost-5-en-17-one, a Neonatal Urinary Metabolite, and the 3,16,18-Triaceate of Its 16&β-Epimer
Das, Rabeya,Kirk, David N.
, p. 1821 - 1831 (2007/10/02)
3β,16α,18-Trihydroxyandrost-5-en-17-one and the triacetate of its 16β-epimer have been synthesized from 3β-hydroxypregna-5,16-dien-20-one via the 'hypoiodite' reaction of the derived 3β-acetoxy-16α,17α-epoxypregn-5-en-20-ols to functionalize C-18, followed by controlled opening of the epoxide ring by reagents chosen to give either 3β,16α,18- or 3β,16β,18-triacetoxy-17α-hydroxypregn-5-en-20-one.Reduction of the 20-oxo group and oxidative cleavage of the C(17) - C(20) bond produced the corresponding 3β,16,18-triacetoxyandrost-5-en-17-one. 3β,16α,18-Trihydroxyandrost-5-en-17-one was obtained by deacetylation of its triacetate, but the 16β-epimer rearranged on hydrolysis to give 3β,17β,18-trihydroxyandrost-5-en-16-one.The androst-5-ene-3β,16,17β,18-tetraols were also prepared.
