(2S,4R)-5-(tert-butyldiphenylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide | 1001208-19-0

• 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: (2S,4R)-5-(tert-butyldiphenylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide
• 英文别名: (2S,4R)-5-[tert-butyl(diphenyl)silyl]oxy-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N,2,4-trimethylpentanamide
• CAS: 1001208-19-0
• 化学式: C₃₃H₄₅NO₃Si
• 分子量: 531.811
• InChiKey: AFYUYVIOJJZUPV-LIGWSQQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4R)-5-(tert-butyldiphenylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 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 (2R,4S)-2,4-dimethyl-1-<(tert-butyldiphenylsilyl)oxy>hex-5-ene
  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：

  (2S)-(tert-butyl)(3-iodo-2-methylpropoxy)diphenylsilane 、 丙酰胺,N-[(1R,2R)-2-羟基-1-甲基-2-苯基乙基]-N-甲基- 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以95%的产率得到(2S,4R)-5-(tert-butyldiphenylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide
  参考文献：
  名称：

  天奇霉素A全功能化无环核心的立体选择性合成

  摘要：

  描述了一种针对大环内酯聚酮化合物天奇霉素 A 的高度收敛的合成方法。我们合成方法的显着特点包括高度立体选择性的迈尔斯烷基化、底物控制的抗羟醛反应和 Masamune-Roush 烯化。

  DOI：

  10.24820/ark.5550190.p010.287

文献信息

• Total Synthesis of (−)-Okilactomycin
  作者：Amos B. Smith、Kallol Basu、Todd Bosanac

  DOI：10.1021/ja077569l

  日期：2007.12.1

  A highly convergent synthesis of (-)-okilactomycin is described. Key reactions of this synthesis include a strategy-level diastereoselective oxy-Cope rearrangement/oxidation sequence, a Petasis-Ferrier union/rearrangement tactic, and an efficient RCM reaction to construct the 13-membered macrocyclic ring.

  描述了 (-)-okilactomycin 的高度收敛合成。该合成的关键反应包括策略级非对映选择性氧-科普重排/氧化序列、Petasis-Ferrier 结合/重排策略以及构建 13 元大环的有效 RCM 反应。
• Smith, Amos B. III; Bosanac, Todd; Basu, Kallol, Journal of the American Chemical Society, 2009, vol. 131, p. 2348 - 2358
  作者：Smith, Amos B. III、Bosanac, Todd、Basu, Kallol

  DOI：——

  日期：——
• Total Synthesis and Biological Evaluation of Tyroscherin
  作者：Hyun Seop Tae、John Hines、Ashley R. Schneekloth、Craig M. Crews

  DOI：10.1021/ol101801u

  日期：2010.10.1

  The efficient synthesis and biological evaluation of both the reported and revised structures of tyroscherin have been achieved. Central to our synthesis is a cross metathesis reaction that generated the trans-olefin regioselectively. This synthetic strategy enabled the facile manipulation of tyroscherin stereochemistry, facilitating the generation of all 16 tyroscherin diastereomers and a photoactivatable tyroscherin-based affinity probe for future mode of action studies.
• Unexpected stereochemical tolerance for the biological activity of tyroscherin
  作者：Hyun Seop Tae、John Hines、Ashley R. Schneekloth、Craig M. Crews

  DOI：10.1016/j.bmc.2011.01.027

  日期：2011.3

  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.
• Stereoselective synthesis of fully functionalized acyclic core of Tianchimycin A
  作者：Yamini Vanipenta、Subhash Ghosh

  DOI：10.24820/ark.5550190.p010.287

  日期：——

  A highly convergent synthetic approach towards the macrolactone polyketide tianchimycin A is described. Notable features of our synthetic approach include highly stereoselective Myers alkylation, substrate controlled anti aldol reaction, and Masamune-Roush olefination.

  描述了一种针对大环内酯聚酮化合物天奇霉素 A 的高度收敛的合成方法。我们合成方法的显着特点包括高度立体选择性的迈尔斯烷基化、底物控制的抗羟醛反应和 Masamune-Roush 烯化。