A New and Convenient Synthesis of 1α,25-Dihydroxyvitamin D2 and Its 24<i>R</i>-Epimer
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- Masahiro Tsuji
- Research Center, Nisshin Flour Milling, Co., Ltd
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- Shinji Yokoyama
- Research Center, Nisshin Flour Milling, Co., Ltd
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- Yoji Tachibana
- Research Center, Nisshin Flour Milling, Co., Ltd
書誌事項
- 公開日
- 1989-10-01
- 権利情報
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- https://academic.oup.com/pages/standard-publication-reuse-rights
- DOI
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- 10.1246/bcsj.62.3132
- 公開者
- Oxford University Press (OUP)
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説明
<jats:title>Abstract</jats:title> <jats:p>1α, 25-Dihydroxyvitamin D2 (1a) was synthesized by irradiation and subsequent thermal isomerization of (22E)-5,7,22-ergostatriene-1α,3β,25-triol (16a). The triol 16a was obtained via 22-oxo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl diacetate (12) starting from (22E)-5,7,22-ergostatriene-1α,3β-diyl diacetate (10), a precursor of 1α-hydroxyvitamin D2. Introduction of the new side chain with the desired stereochemistry was carried out selectively by the reductive elimination of the β-hydroxy sulfone derived from the C-22 aldehyde (12) and an optically active sulfone, prepared via (S)-2,3-dimethyl-1,3-butanediol from methyl (S)-3-hydroxy-2-methylpropionate. Similarly a C-24 epimer of 1a was synthesized.</jats:p>
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 62 (10), 3132-3137, 1989-10-01
Oxford University Press (OUP)
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詳細情報 詳細情報について
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- CRID
- 1360002219103226496
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- NII論文ID
- 130001980733
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- ISSN
- 13480634
- 00092673
- https://id.crossref.org/issn/00092673
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- データソース種別
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