(8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(p-toluenesulfonyl)oxy]methyl-pregnane | 235108-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(p-toluenesulfonyl)oxy]methyl-pregnane
• CAS: 235108-11-9
• 化学式: C₂₆H₄₄O₄SSi
• 分子量: 480.784
• InChiKey: AFHQSLCJLLKIKL-VEGUDHRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(p-toluenesulfonyl)oxy]methyl-pregnane 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (8S,20S)-des-A,B-22,22-dimethyl-cholestane-8β,25-diol
  参考文献：
  名称：

  A 20S Combined with a 22R Configuration Markedly Increases both in Vivo and in Vitro Biological Activity of 1α,25-Dihydroxy-22-methyl-2-methylene-19-norvitamin D₃

  摘要：

  Six new analogues of 1 alpha,25-dihydroxy-19-norvitamin D-3 (3a-4b, 5, and 6) were prepared by a convergent synthesis applying the Wittig-Horner reaction as a key step. The influence of methyl groups at C-22 on their biological activity was examined. It was established that both in vitro and in vivo activity is strongly dependent on the configuration of the stereogenic centers at C-20 and C-22. Introduction of the second methyl group at C-22 (analogues 5 and 6) generates the compounds that are slightly more potent than 1 alpha,25-(OH)(2)D-3 in the in vitro tests but much less potent in vivo. The greatest in vitro and in vivo biological activity was achieved when the C-20 is in the S configuration and the C-22 is in the R configuration. The building blocks for the synthesis, the respective (20R,22R)-, (20R,22S)-, (20S,22R)-, and (20S,22S)-diols, were obtained by fractional crystallization of mixtures of the corresponding diastereomers. Structures and absolute configurations of the diols 21a, 21b, and 22a as well as analogues 3a, 5, and 6 were confirmed by the X-ray crystallography.

  DOI：

  10.1021/jm300187x
• 作为产物：
  描述：

  2-[(1R,3aR,4S,7aR)-7a-methyl-4-triethylsilyloxy-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]propanal 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.75h， 生成 (8S,20R)-des-A,B-8-[(triethylsilyl)oxy]-20-[(p-toluenesulfonyl)oxy]methyl-pregnane
  参考文献：
  名称：

  DIASTEREOMERS OF 2-METHYLENE-19-NOR-22-METHYL-1ALPHA,25-DIHYDROXYVITAMIN D3

  摘要：

  提供了公式I的化合物，其中X1、X2和X3分别选自H或羟基保护基团。这些化合物可用于制备药物组合物，并可用于治疗各种生物状况。

  公开号：

  US20110237557A1

文献信息

• (20S)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-DIHYDROXYVITAMIN D3 AND (20R)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-HYDROXYVITAMIN D3
  申请人：DeLuca Hector F.

  公开号：US20110237556A1

  公开（公告）日：2011-09-29

  Compounds of formula I are provided where X 1 , X 2 and X 3 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

  提供了具有公式I的化合物，其中X1、X2和X3分别选择自H或羟基保护基团。这些化合物可用于制备药物组合物，并可用于治疗各种生物条件。