(S)-5-(benzyloxy)-3-(tert-butyldiphenylsiloxy)pentanal | 106064-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-(benzyloxy)-3-(tert-butyldiphenylsiloxy)pentanal
• 英文别名: 5-(benzyloxy)-3-((tert-butyldiphenylsilyl)oxy)pentanal；5-(benzyloxy)-3-[(tert-butyldiphenylsilyl)oxy]pentanal；(3S)-3-[tert-butyl(diphenyl)silyl]oxy-5-phenylmethoxypentanal
• CAS: 106064-52-2
• 化学式: C₂₈H₃₄O₃Si
• 分子量: 446.662
• InChiKey: UCONCKYMNFAERX-RUZDIDTESA-N

物化性质

• 沸点：
  522.7±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-(benzyloxy)-3-(tert-butyldiphenylsiloxy)pentanal 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 (R)-1-phenylmethoxyoct-7-en-3-ol
  参考文献：
  名称：

  Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of .beta.-keto esters. A (R)- or (S)-1,3,5-trihydroxypentane synthon

  摘要：

  DOI：

  10.1021/jo00378a007
• 作为产物：
  描述：

  5(S)-(benzyloxy)-3-((tert-butyldiphenylsilyl)oxy)pentanol 在 sodium acetate 、 2,2'-bipyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-5-(benzyloxy)-3-(tert-butyldiphenylsiloxy)pentanal
  参考文献：
  名称：

  Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of .beta.-keto esters. A (R)- or (S)-1,3,5-trihydroxypentane synthon

  摘要：

  DOI：

  10.1021/jo00378a007

文献信息

• An asymmetric synthesis of the polyol fragment of the polyene macrolide antibiotic RK-397
  作者：Fan Fu、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2009.03.019

  日期：2009.7

  A highly convergent and asymmetric synthesis of the C11–C31 polyol fragment of RK-397 as a single isomer is accomplished via a catalytic enantioselective hetero-Diels–Alder reaction and an intermolecular olefin cross-metathesis as key steps.

  RK-397的C11–C31多元醇片段作为单一异构体的高度收敛和不对称合成是通过催化对映选择性杂Diels–Alder反应和分子间烯烃交叉复分解反应完成的。
• Design, synthesis, and evaluation of potent bryostatin analogs that modulate PKC translocation selectivity
  作者：Paul A. Wender、Jeremy L. Baryza、Stacey E. Brenner、Brian A. DeChristopher、Brian A. Loy、Adam J. Schrier、Vishal A. Verma

  DOI：10.1073/pnas.1015270108

  日期：2011.4.26

  Modern methods for the identification of therapeutic leads include chemical or virtual screening of compound libraries. Nature’s library represents a vast and diverse source of leads, often exhibiting exquisite biological activities. However, the advancement of natural product leads into the clinic is often impeded by their scarcity, complexity, and nonoptimal properties or efficacy as well as the challenges associated with their synthesis or modification. Function-oriented synthesis represents a strategy to address these issues through the design of simpler and therefore synthetically more accessible analogs that incorporate the activity-determining features of the natural product leads. This study illustrates the application of this strategy to the design and synthesis of functional analogs of the bryostatin marine natural products. It is specifically directed at exploring the activity-determining role of bryostatin A-ring functionality on PKC affinity and selectivity. The resultant functional analogs, which were prepared by a flexible, modular synthetic strategy, exhibit excellent affinity to PKC and differential isoform selectivity. These and related studies provide the basic information needed for the design of simplified and thus synthetically more accessible functional analogs that target PKC isoforms, major targets of therapeutic interest.

  现代识别治疗药物的方法包括化学或虚拟筛选化合物库。自然界的库存代表了一个庞大而多样化的潜在来源，通常表现出精美的生物活性。然而，将天然产物引领进入临床往往受到它们的稀缺性、复杂性、性能或功效的非最优以及与它们的合成或修饰相关的挑战的阻碍。功能定向合成通过设计更简单且因此更易合成的类似物来纠正这些问题，这些类似物包含天然产物引领的活性决定特征。本研究阐述了将这种策略应用于设计和合成海洋天然产物bryostatin的功能类似物的方法。它专门针对探索bryostatin A环功能对PKC亲和力和选择性的活性决定作用。由灵活的模块化合成策略制备的结果功能类似物展现出对PKC的优异亲和力和差异性异构体选择性。这些和相关的研究为设计简化且因此更易合成的靶向PKC异构体的功能类似物所需的基本信息提供了。
• BROOKS D. W.; KELLOGG R. P.; COOPER C. S., J. ORG. CHEM., 52,(1987) N 2, 192-196
  作者：BROOKS D. W.、 KELLOGG R. P.、 COOPER C. S.

  DOI：——

  日期：——
• Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of .beta.-keto esters. A (R)- or (S)-1,3,5-trihydroxypentane synthon
  作者：Dee W. Brooks、Rosemary P. Kellogg、Curt S. Cooper

  DOI：10.1021/jo00378a007

  日期：1987.1