(3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene | 1101867-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene
• CAS: 1101867-37-1
• 化学式: C₂₀H₃₈O₃Si₂
• 分子量: 382.691
• InChiKey: NGQANDLKEDFSFT-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene 、 (3-溴丙氧基)叔丁基二甲基硅烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.17h， 以80%的产率得到(3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-[((3'-tert-butyldimethylsilyl)oxy)propoxy]-1-ethynylcyclohex-1-ene
  参考文献：
  名称：

  Synthesis and biological activity of previtamin D3 analogues with A-ring modifications

  摘要：

  Synthesis of two novel 6-s-cis analogues of 1 alpha,25-dihydroxyvitamin D-3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2b-(3'-hydroxypropoxy) moiety or a 2 beta,3 beta-epoxy group into 1 alpha,25-(OH)2-19-nor-pre-D-3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.053
• 作为产物：
  描述：

  (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde 、 三甲基硅烷化重氮甲烷 在 正丁基锂 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 8.0h， 生成 (3R,4R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene
  参考文献：
  名称：

  Synthesis and biological activity of previtamin D3 analogues with A-ring modifications

  摘要：

  Synthesis of two novel 6-s-cis analogues of 1 alpha,25-dihydroxyvitamin D-3 are described using shikimic acid and its 4-epi isomer as versatile chiral starting materials. These derivatives contain a 2b-(3'-hydroxypropoxy) moiety or a 2 beta,3 beta-epoxy group into 1 alpha,25-(OH)2-19-nor-pre-D-3. The synthesized analogues were found to be not suitable for binding to the vitamin D receptor and showed weak binding affinity toward the vitamin D-binding protein. The new derivatives failed to inhibit cell proliferation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.053