Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Organic Fluorine Compounds. XXXIX. Studies on Steroids. LXXIX. Synthesis of 1α, 25-Dihydroxy-26, 26, 26, 27, 27, 27-hexafluorovitamin D3
小林 義郎田口 武夫三橋 智江口 正大島 悦夫池川 信夫
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1982 年 30 巻 12 号 p. 4297-4303

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1α, 25-Dihydroxy-26, 26, 26, 27, 27, 27-hexafluorocholesterol was synthesized by two procedures. Cholenic acid was converted to the 1α-hydroxy-24-sulfone derivative and hexafluoroacetone was reacted with the lithiated 24-sulfone. Subsequent removal of the sulfonyl group afforded the hexafluoro-1α, 25-dihydroxy compound. An alternative process consists of construction of the hexafluoro-25-hydroxy part on the side chain followed by the introduction of a hydroxy group at the 1α-position. The hexafluoro derivative was converted to the vitamin D form, 1α, 25-dihydroxyhexafluorovitamin D3, via the corresponding 5, 7-diene.
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© The Pharmaceutical Society of Japan
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