Syntheses of 22,23-dihydro-1.ALPHA.,25-dihydroxyvitamin D2 and its 24R-epimer, new vitamin D2 derivatives.
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概要
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New 1α,25-dihydroxy vitamin D<SUB>2</SUB> derivatives (22,23-dihydro-1α,25-dihydroxyvitamin D<SUB>2</SUB> (<B>2a</B>)) and its 24<I>R</I>-epimer (<B>2b</B>), were synthesized by two procedures. 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>8</B>), obtainable readily from ergosterol, was converted to 22-phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinor-6-cholene (<B>14</B>) or 22-iodo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinor-6-cholene (<B>16</B>). Condensation of the C-22 sulfone (<B>14</B>) with (3<I>R</I>)-4-iodo-2,3-dimethyl-2-butanol THP ether, or the C-22 iodide (<B>16</B>) with (3<I>R</I>)-2,3-dimethyl-4-phenylsulfonyl-2-butanol THP ether followed by desulfonylation and successive deprotection gave 5,7-ergostadiene-1α,3β,25-triol (<B>21a</B>), which led to <B>2a</B> upon irradiation and subsequent thermal isomerization. Similarly, a 24<I>R</I>-epimer of <B>2a</B> was synthesized.
- 公益社団法人 日本化学会の論文
著者
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Yokoyama Shinji
Research Center, Nisshin Flour Milling, Co., Ltd.
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Tsuji Masahiro
Research Center, Nisshin Flour Milling, Co., Ltd.
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Tachibana Yoji
Research Center, Nisshin Flour Milling, Co., Ltd.
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Ikekawa Nobuo
Iwaki Meisei University
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- 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.