(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-(methanesulfonyloxy)cyclohex-1-ene | 1101867-33-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-(methanesulfonyloxy)cyclohex-1-ene
• CAS: 1101867-33-7
• 化学式: C₂₁H₄₀O₅SSi₂
• 分子量: 460.783
• InChiKey: ZVPCVLFFPZQXBV-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-(methanesulfonyloxy)cyclohex-1-ene 、 25-trimethylsilyloxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate 在 copper(l) iodide 、 二乙酰二(三苯基膦)钯 、 二乙胺 作用下， 反应 4.0h， 生成
  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,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-hydroxycyclohex-1-ene 、 甲基磺酰氯 在 吡啶 作用下， 反应 2.0h， 以89%的产率得到(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-1-ethynyl-4-(methanesulfonyloxy)cyclohex-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