Stereoselective syntheses of (22R)- and (22S)-22-methyl-1.alpha.,25-dihydroxyvitamin D3: active vitamin D3 analogs with restricted side-chain conformation
Stereoselective syntheses of (22R)- and (22S)-22-methyl-1.alpha.,25-dihydroxyvitamin D3: active vitamin D3 analogs with restricted side-chain conformation
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(22R)- 和 (22S)-22-甲基-1.α.,25-二羟基维生素 D3 的立体选择性合成：具有受限侧链构象的活性维生素 D3 类似物
DOI：
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发表时间：
1993
期刊：
影响因子：
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通讯作者：
H. DeLuca
中科院分区：
文献类型：
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作者：
Keiko Yamamoto;J. Takahashi;K. Hamano;S. Yamada;K. Yamaguchi;H. DeLuca
以1α-羟基化C（22）-甾体2为原料，立体选择性地合成了（22 R）-和（22 S）-22-甲基-1 α，25-二羟基维生素D3（1b和1c）。这两种新的维生素D类似物具有一个灵活性有限的侧链，旨在研究与活性维生素D 3（VDR）受体结合所需的立体化学结构。力场计算表明，（22 R）-和（22 S）-甲基化活性维生素D3类似物（1b和1c）的侧链在C（17-20-22-23）二面角上分别以90%以上的群体偏（+）和反（anti）构象存在
(22R)- and (22S)-22-methyl-1α,25-dihydroxyvitamin D 3 (1b and 1c) were synthesized stereoselectively from 1α-hydroxylated C(22)-steroid 2. The two new vitamin D analogs, which have a side chain with restricted flexibility, were designed to allow the study of the stereochemical structure required to bind to the receptor of the active vitamin D 3 (VDR). According to force-field calculations, the side chain of (22R)- and (22S)-methylated active vitamin D 3 analogs (1b and 1c) adopts with more than 90% of the population gauche(+) and anti conformations, respectively, at the C(17-20-22-23) dihedral angle