(2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol | 730964-35-9

• 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: (2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol
• 英文别名: (2R,4R)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentan-1-ol
• CAS: 730964-35-9
• 化学式: C₂₃H₃₄O₂Si
• 分子量: 370.607
• InChiKey: NBIHJOZBHSUWNL-WOJBJXKFSA-N

物化性质

• 沸点：
  433.6±37.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  26
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol 在 正丁基锂 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027
• 作为产物：
  描述：

  (2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 在 LAB 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4R)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol
  参考文献：
  名称：

  Unexpected stereochemical tolerance for the biological activity of tyroscherin

  摘要：

  Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.027

文献信息

• Biakamides A–D, Unique Polyketides from a Marine Sponge, Act as Selective Growth Inhibitors of Tumor Cells Adapted to Nutrient Starvation
  作者：Naoyuki Kotoku、Ryosuke Ishida、Hirokazu Matsumoto、Masayoshi Arai、Kazunari Toda、Andi Setiawan、Osamu Muraoka、Motomasa Kobayashi

  DOI：10.1021/acs.joc.6b02948

  日期：2017.2.3

  configuration of the secondary alcohol moiety in biakamides A and B, the absolute stereostructures of the two secondary methyl groups in biakamides A–D were determined by the asymmetric total syntheses of all possible stereoisomers from the optically pure monoprotected 2,4-dimethyl-1,5-diol. Biakamides A–D showed selective antiproliferative activities against PANC-1 cells cultured under glucose-deficient

  Biakamides A–D是一种新型的异常独特的聚酮化合物，它是使用PANC-1人胰腺癌细胞从印尼海洋海绵（Petrosaspongia sp。）中进行构建的生物测定法分离得到的。通过对联氨酰胺的一维和二维NMR光谱的详细分析，平面化学结构具有末端噻唑，两个N获得了-甲基酰胺，氯亚甲基和取代的丁酰基部分。阐明了联氨酰胺A和B中仲醇部分的构型后，联氨酰胺A–D中两个仲甲基的绝对立体结构是由光学纯的单保护2,4-化合物中所有可能的立体异构体的不对称总合成确定的1，5-二甲基二醇。Biakamides A–D对在葡萄糖缺乏条件下以浓度依赖性方式培养的PANC-1细胞表现出选择性的抗增殖活性。发现Biakamides的主要作用方式是抑制线粒体电子传输链中的复合物I。
• α,ω-Functionalized 2,4-Dimethylpentane Dyads and 2,4,6-Trimethylheptane Triads through Asymmetric Hydrogenation
  作者：Jianguang Zhou、Kevin Burgess

  DOI：10.1002/anie.200603635

  日期：2007.2.5
• An Efficient and General Method for the Synthesis ofα,ω-Difunctional Reduced Polypropionates by Zr-Catalyzed Asymmetric Carboalumination: Synthesis of the Scyphostatin Side Chain
  作者：Ze Tan、Ei-ichi Negishi

  DOI：10.1002/anie.200353429

  日期：2004.5.24