tert-butyl (4S)-4-[(2S,3S)-3-[(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]pentanoate | 127807-72-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4S)-4-[(2S,3S)-3-[(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]pentanoate
• CAS: 127807-72-1
• 化学式: C₂₅H₄₄O₆
• 分子量: 440.621
• InChiKey: GMXBITBEOGQWJL-GPHNJDIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-[(2S,3S)-3-[(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]pentanoate 在 盐酸 、 叔丁基过氧化氢 、 三甲基氯硅烷 、 bis(acetylacetonate)oxovanadium 、 18-冠醚-6 、 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 205.17h， 生成 (3R,4R)-4-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-3-cyano-1-hydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-4-hydroxy-3-methylbutanenitrile
  参考文献：
  名称：

  Enantioselective complexation of organic ammonium ions by simple tetracyclic podand ionophores

  摘要：

  A series of enantiomerically pure, C2-symmetric tetracyclic podands are synthesized and studied. These host molecules have methyl substitution, which allows only a few low-energy conformations, and they form well-defined complexes with chiral ammonium salts. With derivatives of alpha-phenethylammonium hexafluorophosphate as guests, binding enantioselectivity ranges from approximately 0 to 60% ee. X-ray structures of several podand/chiral ammonium perchlorate complexes are described along with a conformational analysis of the podands and their complexes.

  DOI：

  10.1021/ja00037a014
• 作为产物：
  描述：

  2-((2R,3S)-3-Isopropenyl-1,4-dioxa-spiro[4.4]non-2-yl)-propan-2-ol 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 氯化亚砜 、 双氧水 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 六甲基磷酰三胺 、 丙酮 为溶剂， 生成 tert-butyl (4S)-4-[(2S,3S)-3-[(2S)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentan-2-yl]-1,4-dioxaspiro[4.4]nonan-2-yl]pentanoate
  参考文献：
  名称：

  Enantioselective Complexation with a Conformationally Homogeneous C2 Podand Ionophore

  摘要：

  DOI：

  10.1016/s0040-4039(01)93394-5

文献信息

• On the stereochemical control of complexation in tetrahydropyranoid podand ionophores
  作者：Shawn D. Erickson、W. Clark Still

  DOI：10.1016/s0040-4039(00)97593-2

  日期：——

  To test a proposal that stereochemistry can be used rationally to control the binding properties of ionophores, a new podand (3) has been prepared and studied. Unlike the previously prepared stereoisomeric podand 2 which has substitution and stereochemistry which enforces a single tetradentate binding conformation, 3 has been designed to avoid conformations in which all four oxygens can simultaneously

  为了检验可以合理地使用立体化学来控制离子载体的结合特性的提议，已经制备并研究了新的荚果（3）。不同于先前制备的立体异构荚醚2具有取代和立体化学，其强制单个四齿结合构象，3已被设计为避免构象，其中所有四个氧可以同时使用离子坐标。
• Improved Synthesis of Functionalized Podand Ionophores
  作者：Matthew T. Burger、W. Clark Still

  DOI：10.1021/jo9515438

  日期：1996.1.1
• Enantioselective complexation of organic ammonium ions by simple tetracyclic podand ionophores
  作者：Xuebao Wang、Shawn D. Erickson、Takamasa Iimori、W. Clark Still

  DOI：10.1021/ja00037a014

  日期：1992.5

  A series of enantiomerically pure, C2-symmetric tetracyclic podands are synthesized and studied. These host molecules have methyl substitution, which allows only a few low-energy conformations, and they form well-defined complexes with chiral ammonium salts. With derivatives of alpha-phenethylammonium hexafluorophosphate as guests, binding enantioselectivity ranges from approximately 0 to 60% ee. X-ray structures of several podand/chiral ammonium perchlorate complexes are described along with a conformational analysis of the podands and their complexes.
• Enantioselective Complexation with a Conformationally Homogeneous C2 Podand Ionophore
  作者：Takamasa Iimori、Shawn D. Erickson、Arnold L. Rheingold、W.Clark Still

  DOI：10.1016/s0040-4039(01)93394-5

  日期：——