Studies on 1α-Hydroxyl Derivatives of Vitamin D_3. I. : Syntheses of 1α-Hydroxyvitamin D_3 and 1α, 25-Dihydroxyvitamin D_3
スポンサーリンク
概要
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1α-Hydroxyvitamin D_3 (XIVa) was synthesized from cholesterol (Ia) in ca. 1.5% overall yield. 1α, 2α-Epoxycholest-4-en-3-one (IVa) readily obtained from Ia was converted to 1α, 2α-epoxycholest-5-en-3-one (Va) by the modified deconjugation reaction with t-BuOK in DMSO. Reduction of Va with Ca (BH_4)_2 and then with LiAlH_4 gave 1α-hydroxycholesterol (VIIIa) in 15.6% yield from Ia. Allylic bromination and subsequent dehydrobromination of the diacetate of VIIIa afforded 1α, 3β-diacetoxycholesta-5,7-diene (XIa), whose saponification gave the corresponding diol (XIIa). 1α-Hydroxyprovitamin D_3 (XIIa) in ethanol was irradiated with the ultraviolet lights in the range between 275 and 310 nm through a newly found filter solution. The formed 1α-hydroxyprevitamin D_3 (XIIIa) was thermally isomerized into 1α-hydroxyvitamin D_3. The yield of XIVa from XIIa was ca. 25%. These procedures were applied to 25-hydroxycholesterol (Ib) and 1α, 25-dihydroxyvitamin D_3 (XIVb) was obtained ca. 0.4% overall yield from Ib.
- 社団法人日本薬学会の論文
- 1978-10-25
著者
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小林 正
Department Of Biochemistry Kobe Gakuin University
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辻井 昌彦
Eisai Chemical Co. Ltd.
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里 忠
Tsukuba Research Laboratories Eisai Co. Ltd.
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国井 敏信
Tsukuba Research Laboratories, Eisai Co., Ltd.
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山内 博
エーザイ(株)
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影井 健吾
エーザイ株式会社研究開発本部
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影井 健吾
Research and Development Division, Eisai Co., Ltd.
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豊島 昭二
Research and Development Division, Eisai Co., Ltd.
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国井 敏信
Tsukuba Research Laboratories Eisai Co. Ltd.
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豊島 昭二
エーザイ株式会社研究開発本部
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緒方 善武
エーザイ株式会社研究開発本部
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影井 健吾
Research and Development Division, Eisai Co., Ltd
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豊島 昭二
Research and Development Division, Eisai Co., Ltd
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