Bile Acids and Steroids. XVII. Thiosteroids. (6). Synthesis of 16β-Mercapto-17α-hydroxyprogesterone and 16β-Mercaptotestosterone
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概要
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Some 16α, 17α-epoxy-steroids were converted to the corresponding thiocyanato-hydrins, (II), (IVa), (IVb), and (VI). Oxime-formation reaction of 3β, 17α-dihydroxy-16β-thiocyanato-5-pregnen-20-one 3-acetate (IVb) yielded a mixture of the oxime-thiol (IXa) and the oxime-disulfide (IX). These structures were assumed by identification of the Beckmann rearrangement products, (X) and (XI). Dehydration of the Beckmann rearragement by-product (XI) gave a base (XVI), which was assumed to be 2'-methylthiazolo [5', 4'-16,17] androsta-5,16-dien-3β-ol 3-acetate from the consideration of the mechanism of the Beckmann rearrangement. From the normal. product (X), 16β-mercapto-17β-hydroxy-4-androsten-3-one 16,17-acetonide (XIX) was synthesized in three steps.
- 公益社団法人日本薬学会の論文
- 1960-08-25
著者
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米野 太一郎
Research Laboratory, Shionogi & Co., Ltd.
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米野 太一郎
Shionogi Research Laboratory Shionogi & Co. Ltd.
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