A new and convenient synthesis of 1.ALPHA.,25-dihydroxyvitamin D2 and its 24R-epimer.

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概要

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• 1α, 25-Dihydroxyvitamin D<SUB>2</SUB> (<B>1a</B>) was synthesized by irradiation and subsequent thermal isomerization of (22<I>E</I>)-5,7,22-ergostatriene-1α,3β,25-triol (<B>16a</B>). The triol <B>16a</B> 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 (<B>12</B>) starting from (22<I>E</I>)-5,7,22-ergostatriene-1α,3β-diyl diacetate (<B>10</B>), a precursor of 1α-hydroxyvitamin D<SUB>2</SUB>. 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 (<B>12</B>) and an optically active sulfone, prepared via (<I>S</I>)-2,3-dimethyl-1,3-butanediol from methyl (<I>S</I>)-3-hydroxy-2-methylpropionate. Similarly a C-24 epimer of <B>1a</B> was synthesized.

• 公益社団法人 日本化学会の論文

著者

• Yokoyama Shinji

  Research Center, Nisshin Flour Milling, Co., Ltd.

• Tsuji Masahiro

  Research Center, Nisshin Flour Milling, Co., Ltd.

• Tachibana Yoji

  Research Center, Nisshin Flour Milling, Co., Ltd.

関連論文

• Efficacy of Therapeutic Angiogenesls by Autologous Bone Marrow Cell Transplantation for Buerger's Disease
• Syntheses of 22,23-dihydro-1.ALPHA.,25-dihydroxyvitamin D2 and its 24R-epimer, new vitamin D2 derivatives.
• A new and convenient synthesis of 1.ALPHA.,25-dihydroxyvitamin D2 and its 24R-epimer.

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