(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxy-1-hydroxymethylcyclohex-1-ene | 1101867-40-6

• 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,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxy-1-hydroxymethylcyclohex-1-ene
• CAS: 1101867-40-6
• 化学式: C₁₉H₄₀O₄Si₂
• 分子量: 388.695
• InChiKey: VLJRRBPAXJTTQE-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxy-1-hydroxymethylcyclohex-1-ene 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarbaldehyde
  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：

  Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate 在 二异丁基氢化铝 、 水 、 Rochelle's salt 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以75%的产率得到(3R,4S,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-4-hydroxy-1-hydroxymethylcyclohex-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