1-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)butan-3-one | 108744-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)butan-3-one
• 英文别名: 4-[(2R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butan-2-one
• CAS: 108744-02-1
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: JYTPVJUCSASUSW-VTMRUAGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  生成 1-(3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)butan-3-one
  参考文献：
  名称：

  HUTCHINSON, D. K.;FUCHS, P. L., J. AMER. CHEM. SOC., 109,(1987) N 16, 4930-4939

  摘要：

  DOI：

文献信息

• Functionalized olefin cross-coupling to construct carbon–carbon bonds
  作者：Julian C. Lo、Jinghan Gui、Yuki Yabe、Chung-Mao Pan、Phil S. Baran

  DOI：10.1038/nature14006

  日期：2014.12.18

  Carbon–carbon (C–C) bonds form the backbone of many important molecules, including polymers, dyes and pharmaceutical agents. The development of new methods to create these essential connections in a rapid and practical fashion has been the focus of numerous organic chemists. This endeavour relies heavily on the ability to form C–C bonds in the presence of sensitive functional groups and congested structural environments. Here we report a chemical transformation that allows the facile construction of highly substituted and uniquely functionalized C–C bonds. Using a simple iron catalyst, an inexpensive silane and a benign solvent under ambient atmosphere, heteroatom-substituted olefins are easily reacted with electron-deficient olefins to create molecular architectures that were previously difficult or impossible to access. More than 60 examples are presented with a wide array of substrates, demonstrating the chemoselectivity and mildness of this simple reaction. Highly substituted carbon–carbon bonds are constructed using a simple iron catalyst and an inexpensive silane: more than 60 examples of this reaction — in which heteroatom-substituted olefins are reacted with electron-deficient olefins — are presented. This paper reports the development of a new type of carbon–carbon bond forming reaction that allows for the simple construction of molecules that were previously either impossible or laborious to access. The procedure exploits an interaction between heteroatom-substituted olefins and electron-deficient olefins to construct highly substituted carbon–carbon bonds using a simple iron catalyst and an inexpensive silane. The authors present than sixty examples of this reaction, covering a broad range of substrates. This reaction is of relevance to the design of organic compounds including polymers, dyes, and pharmaceutical agents and semiconductors.

  碳-碳（C-C）键构成了许多重要分子（包括聚合物、染料及医药制剂）的骨架。大量有机化学家致力于开发新的方法，以期能快速高效地制备这些重要的C-C键。该研究项目更多地依赖于在某些特殊的官能团及空间位阻的环境下形成C-C键的能力。本文报道了一种化学转变过程，这一进程使得传统方法难以形成的具有高度空间位阻及特殊官能团的C-C键能够简易地构建出来。通过使用简便的铁基催化剂，廉价的硅烷及环保的溶剂，在常温常压条件下，很容易使一些含有杂原子的烯烃与那些缺电子的烯烃反应，进而形成一些以往在技术上很难实现甚至无法实现的分子结构。超过60种底物的实验数据的展示，表明了这一简便反应所具有的选择性及温和性。通过简便的铁基催化剂及廉价的硅烷，高度取代的碳-碳键被构建出来。超过60种例子探究了这种反应——含有杂原子的烯烃与那些缺电子的烯烃的反应。本文报道了一种新型的C-C键形成反应，该反应使得一些过去在技术上无法实现或极难实现的分子结构能够简单地构建出来。这一过程利用了含有杂原子的烯烃与缺电子烯烃的相互作用，通过简便的铁基催化剂及廉价的硅烷构建出高度取代的C-C键。超过60种实验例子，广泛地展示了这一过程的通用性。这一反应与包括聚合物、染料及医药制剂，半导体等领域有机化合物的合成息息相关。
• Amelioration of the conjugate addition chemistry of .alpha.-alkoxycopper reagents: application to the stereospecific synthesis of C-Glycosides
  作者：D. K. Hutchinson、P. L. Fuchs

  DOI：10.1021/ja00250a029

  日期：1987.8
• HUTCHINSON, D. K.;FUCHS, P. L., J. AMER. CHEM. SOC., 109,(1987) N 16, 4930-4939
  作者：HUTCHINSON, D. K.、FUCHS, P. L.

  DOI：——

  日期：——