(3R,4S,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene | 943970-20-5

• 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: (3R,4S,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene
• CAS: 943970-20-5
• 化学式: C₂₆H₅₂O₃Si₃
• 分子量: 496.954
• InChiKey: LCDRPLBVTXNPFJ-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.12
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene 、 25-trimethylsilyloxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate 在 bis(triphenylphosphine) palladium (Il) acetate copper(l) iodide 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of new 6-s-cis locked 1,2,25-trihydroxyprevitamin D3 analogues

  摘要：

  An efficient synthesis of several diastereomers of 2-hydroxy substituted 1 alpha,25-dihydroxyprevitamin D-3 derivatives was accomplished utilizing a practical route to the A-ring synthon. The biological activity of the analogues was evaluated in vitro. All the synthesized derivatives demonstrated low affinity for the vitamin D receptor and vitamin D-binding protein compared with 1 alpha,25-dihydroxyvitamin D-3, the natural hormone. 1 alpha,2 beta,25-trihydroxy-19-nor-pre-D-3 was the most potent of the analogues in inhibiting proliferation of MCF-7 cells but requires higher EC50 concentrations than lot,25-dihydroxyvitamin D-3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.058
• 作为产物：
  描述：

  (3R,4S,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-(2,2-dibromoethenyl)cyclohex-1-ene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以65%的产率得到(3R,4S,5S)-3,4,5-tri[(tert-butyldimethylsilyl)oxy]-1-ethynylcyclohex-1-ene
  参考文献：
  名称：

  Synthesis and biological evaluation of new 6-s-cis locked 1,2,25-trihydroxyprevitamin D3 analogues

  摘要：

  An efficient synthesis of several diastereomers of 2-hydroxy substituted 1 alpha,25-dihydroxyprevitamin D-3 derivatives was accomplished utilizing a practical route to the A-ring synthon. The biological activity of the analogues was evaluated in vitro. All the synthesized derivatives demonstrated low affinity for the vitamin D receptor and vitamin D-binding protein compared with 1 alpha,25-dihydroxyvitamin D-3, the natural hormone. 1 alpha,2 beta,25-trihydroxy-19-nor-pre-D-3 was the most potent of the analogues in inhibiting proliferation of MCF-7 cells but requires higher EC50 concentrations than lot,25-dihydroxyvitamin D-3. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.058