(4S,5S)-4-hydroxy-5-(2-phenylethynyl)oxolan-2-one | 178977-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S,5S)-4-hydroxy-5-(2-phenylethynyl)oxolan-2-one
• CAS: 178977-50-9
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: UZRWHYWHEPNHFK-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-hydroxy-5-(2-phenylethynyl)oxolan-2-one 在 吡啶 、 4-二甲氨基吡啶 、 (苯并三唑-1-基氧基)二哌啶碳鎓六氟磷酸盐 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 草酰氯 、 trichlorobenzoyl chloride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 21.33h， 生成 Cryptophycin 4
  参考文献：
  名称：

  Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives

  摘要：

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

  DOI：

  10.1021/jo960816b
• 作为产物：
  描述：

  lithium phenylacetylide 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.33h， 生成 (4S,5S)-4-hydroxy-5-(2-phenylethynyl)oxolan-2-one
  参考文献：
  名称：

  Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives

  摘要：

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.

  DOI：

  10.1021/jo960816b

文献信息

• Synthesis and in vitro cytotoxicity of cryptophycins and related analogs
  作者：Jean-Marc de Muys、Rabindra Rej、Dieu Nguyen、Brian Go、Samuel Fortin、Jean-François Lavallée

  DOI：10.1016/0960-894x(96)00182-5

  日期：1996.5

  Several members of the Cryptophycin family were synthesised using a straightforward convergent approach, The proposed synthetic route was used to prepare novel analogs of Cryptophycins A and B in which the benzylic epoxide moiety was replaced by alternate electrophilic functions. The effect of these modifications on cytotoxic activity was determined on several tumor cell lines. (C) 1996 Elsevier Science Ltd
• Total Synthesis of Cryptophycins and Their 16-(3-Phenylacryloyl) Derivatives
  作者：Rabindra Rej、Dieu Nguyen、Brian Go、Samuel Fortin、Jean-François Lavallée

  DOI：10.1021/jo960816b

  日期：1996.1.1

  Cryptophycin A, a cyclic depsipeptide isolated from the blue-green alga (cyanobacterium) Nostoc sp.GSV 224, has shown excellent activity against solid tumors implanted in mice. The benzylic epoxide, which was shown to be very important for biological, activity, is also fairly unstable under both acidic and alkaline conditions. The high doses needed to observe in vivo activity might be a result of this instability. In order to solve this problem while preserving the electrophilic character of the benzylic position, enones 1 and 2 have been proposed as promising analogs of the natural product, and a convergent total synthesis of these compounds is described. In addition, the same strategy was used to prepare Cryptophycins A, B, C, and D.