(22S)-25-<(tert-butyldimethylsilyl)oxy>-22-hydroxy-de-A,B-cholest-23-yn-8β-yl benzoate | 142700-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (22S)-25-<(tert-butyldimethylsilyl)oxy>-22-hydroxy-de-A,B-cholest-23-yn-8β-yl benzoate
• 英文别名: (22S)-25-[(tert-butyldimethylsilyl)oxy]-22-hydroxy-de-A,B-cholest-23-yn-8β-yl benzoate；[(1R,3aR,4S,7aR)-1-[(2S,3S)-6-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 142700-23-0；142760-19-8
• 化学式: C₃₁H₄₈O₄Si
• 分子量: 512.805
• InChiKey: MVUBTLFMLLENOE-SFICGMITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (22S)-25-<(tert-butyldimethylsilyl)oxy>-22-hydroxy-de-A,B-cholest-23-yn-8β-yl benzoate 、 苯次磺酰氯 在 三乙胺 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 2.0h， 以73%的产率得到(22S)-25-<(tert-butyldimethylsilyl)oxy>-24-(phenylsulfinyl)-de-A,B-cholesta-22,23-dien-8β-yl benzoate
  参考文献：
  名称：

  Studies of vitamin D (calciferol) and its analogs. 43. Two novel allenic side chain analogs of 1.alpha.,25-dihydroxyvitamin D3

  摘要：

  Two new analogues of the steroid hormone 1-alpha,25-dihydroxyvitamin D3 (1) in which allenic functionality has been incorporated into the side chain have been synthesized. Both the 22S and 22R allene analogues (2a and 2b) were each separately synthesized in nine steps from a common precursor 9. While both analogues exhibited significant binding to the 1-alpha,25-dihydroxyvitamin D3 chick intestinal receptor, they showed low in vivo activity in stimulating intestinal calcium absorption in the chick.

  DOI：

  10.1021/jo00042a013
• 作为产物：
  描述：

  (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 在 吡啶 、 2,4,6-三甲基吡啶 、 正丁基锂 作用下， 以 二甲基亚砜 为溶剂， 反应 1.25h， 生成 (22S)-25-<(tert-butyldimethylsilyl)oxy>-22-hydroxy-de-A,B-cholest-23-yn-8β-yl benzoate
  参考文献：
  名称：

  Studies of vitamin D (calciferol) and its analogs. 43. Two novel allenic side chain analogs of 1.alpha.,25-dihydroxyvitamin D3

  摘要：

  Two new analogues of the steroid hormone 1-alpha,25-dihydroxyvitamin D3 (1) in which allenic functionality has been incorporated into the side chain have been synthesized. Both the 22S and 22R allene analogues (2a and 2b) were each separately synthesized in nine steps from a common precursor 9. While both analogues exhibited significant binding to the 1-alpha,25-dihydroxyvitamin D3 chick intestinal receptor, they showed low in vivo activity in stimulating intestinal calcium absorption in the chick.

  DOI：

  10.1021/jo00042a013

文献信息

• Studies of vitamin D (calciferol) and its analogs. 43. Two novel allenic side chain analogs of 1.alpha.,25-dihydroxyvitamin D3
  作者：Andrew S. Craig、Anthony W. Norman、William H. Okamura

  DOI：10.1021/jo00042a013

  日期：1992.7

  Two new analogues of the steroid hormone 1-alpha,25-dihydroxyvitamin D3 (1) in which allenic functionality has been incorporated into the side chain have been synthesized. Both the 22S and 22R allene analogues (2a and 2b) were each separately synthesized in nine steps from a common precursor 9. While both analogues exhibited significant binding to the 1-alpha,25-dihydroxyvitamin D3 chick intestinal receptor, they showed low in vivo activity in stimulating intestinal calcium absorption in the chick.