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A method was developed for opening the oxide ring of the 3-acetate of 16α, 17α-epoxy-Δ5-pregnen-3β-ol-20-one with thiolacetic acid under ionic conditions.
The reaction proceeds with a predominant cleavage of the C16-O bond of the oxide ring and attack of the C16-center by the thiolacetic acid in the thiono form, with the formation of the 3-acetate, 16-thionoacetate of Δ5-pregnene-3β, 16β,17α-triol-20-one, the structure of which was assigned on the basis of the sum of the chemical and physicochemical methods.
A small amount (~ 6%) of the isomeric product of opening the ring is formed, which apparently arises as the result of the cleavage of the C17-O bond of the starting oxide by the thiol form of thiolacetic acid.
KeywordsOxide Steroid Thiol Ionic Condition Physicochemical Method
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