(22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-22,23-dien-8β-ol | 142700-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-22,23-dien-8β-ol
• CAS: 142700-26-3
• 化学式: C₂₄H₄₄O₂Si
• 分子量: 392.698
• InChiKey: YRGBGKHDFOMSMC-MSNOBZHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-22,23-dien-8β-ol 在 重铬酸吡啶 、 三氟乙酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以80%的产率得到(22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-22,23-dien-8-one
  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：

  (22R)-25-<(tert-butyldimethylsilyl)oxy>-24-(phenylsulfinyl)-de-A,B-cholesta-22,23-dien-8β-yl benzoate 在 叔丁基锂 作用下， 以 甲醇 、 乙醚 、 正戊烷 为溶剂， 反应 0.17h， 以50%的产率得到(22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-22,23-dien-8β-ol
  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