(22S)-1α,25-bis<(tert-butyldimethylsilyl)oxy>-6,7,22,23,23,24-hexadehydroprevitamin D3 tert-butyldimethylsilyl ether | 142700-21-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (22S)-1α,25-bis<(tert-butyldimethylsilyl)oxy>-6,7,22,23,23,24-hexadehydroprevitamin D3 tert-butyldimethylsilyl ether
• CAS: 142700-21-8
• 化学式: C₄₅H₈₀O₃Si₃
• 分子量: 753.385
• InChiKey: HTDUKQUANISUQR-XMJJXTTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.78
• 重原子数：
  51.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (3S,5R)-3,5-Bis[[dimethyl(1,1-dimethylethyl)silyl]oxy]-1-ethinyl-2-methyl-1-cyclohexene 、 (22S)-25-<(tert-butyldimethylsilyl)oxy>-de-A,B-cholesta-8,22,23-trien-8-yl trifluoromethanesulfonate 在 copper(l) iodide 、 二乙酰二(三苯基膦)钯 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以75%的产率得到(22S)-1α,25-bis<(tert-butyldimethylsilyl)oxy>-6,7,22,23,23,24-hexadehydroprevitamin D3 tert-butyldimethylsilyl ether
  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