(R)-1-(3-((tert-butyldimethylsilyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol | 1013621-67-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-1-(3-((tert-butyldimethylsilyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol
• 英文别名: (R)-1-(3-(tert-butyldimethylsilyloxy)phenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol；(1R)-1-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-(3,4-dimethoxyphenyl)propan-1-ol
• CAS: 1013621-67-4
• 化学式: C₂₃H₃₄O₄Si
• 分子量: 402.606
• InChiKey: CQTSHKFKOPDWAO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-(3-((tert-butyldimethylsilyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol 、 [S-(R*,R*)]-1-[1-氧代-2-(3,4,5-三甲氧基苯基)丁基]-2-哌啶羧酸 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of Shld Derivatives, Their Binding to the Destabilizing Domain, and Influence on Protein Accumulation in Transgenic Plants

  摘要：

  A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly inside or outside the receptor binding site with the latter being important by influencing the overall polarity of the compounds in order to improve the absorption in plants. The binding of the new compounds to the destabilizing domain was determined using a fluorescence polarization competition assay, and the GFP expression in engineered Arabidopsis thaliana was studied. The results showed that modifications of the C-building block phenol with acidic, basic, and neutral groups led to better ligands with some being better than Shld in the plant. Generally small, polar substituents showed the best GFP accumulation.

  DOI：

  10.1021/acs.jmedchem.9b00497
• 作为产物：
  描述：

  (R)-3-(3-(3,4-dimethoxyphenyl)-1-hydroxypropyl)phenol 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到(R)-1-(3-((tert-butyldimethylsilyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Synthesis of Shld Derivatives, Their Binding to the Destabilizing Domain, and Influence on Protein Accumulation in Transgenic Plants

  摘要：

  A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly inside or outside the receptor binding site with the latter being important by influencing the overall polarity of the compounds in order to improve the absorption in plants. The binding of the new compounds to the destabilizing domain was determined using a fluorescence polarization competition assay, and the GFP expression in engineered Arabidopsis thaliana was studied. The results showed that modifications of the C-building block phenol with acidic, basic, and neutral groups led to better ligands with some being better than Shld in the plant. Generally small, polar substituents showed the best GFP accumulation.

  DOI：

  10.1021/acs.jmedchem.9b00497

文献信息

• Synthesis and analysis of stabilizing ligands for FKBP-derived destabilizing domains
  作者：Joshua S. Grimley、Denise A. Chen、Laura A. Banaszynski、Thomas J. Wandless

  DOI：10.1016/j.bmcl.2007.11.044

  日期：2008.1

  We recently identified mutants of the human FKBP12 protein that are unstable and rapidly degraded when expressed in mammalian cells. We call these FKBP mutants destabilizing domains (DDs), because their instability is conferred to any protein fused to the DDs. A cell-permeable ligand binds tightly to the DDs and prevents their degradation, thus providing small molecule control over intracellular protein levels. We now report the synthesis and functional characterization of a stabilizing ligand called Shield-2. The synthesis of Shield-2 is efficient, and this ligand binds to the FKBP(F36V) protein with a dissociation constant of 29 nM. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of <b>Shld</b> Derivatives, Their Binding to the Destabilizing Domain, and Influence on Protein Accumulation in Transgenic Plants
  作者：Frederik Præstholm Jørgensen、Daniel Madsen、Morten Meldal、Jacob Valdbjørn Olsen、Morten Petersen、Jeppe Granhøj、Mikael Bols

  DOI：10.1021/acs.jmedchem.9b00497

  日期：2019.5.23

  A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly inside or outside the receptor binding site with the latter being important by influencing the overall polarity of the compounds in order to improve the absorption in plants. The binding of the new compounds to the destabilizing domain was determined using a fluorescence polarization competition assay, and the GFP expression in engineered Arabidopsis thaliana was studied. The results showed that modifications of the C-building block phenol with acidic, basic, and neutral groups led to better ligands with some being better than Shld in the plant. Generally small, polar substituents showed the best GFP accumulation.