(1R,2R)-1-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-1,3-dihydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-2-methylpropane-1,3-diol | 140465-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R,2R)-1-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-1,3-dihydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-2-methylpropane-1,3-diol
• CAS: 140465-00-5
• 化学式: C₂₀H₃₈O₆
• 分子量: 374.518
• InChiKey: RJNNYWQFRMZMFF-DLZZHKMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-1,3-dihydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-2-methylpropane-1,3-diol 在 盐酸 、 氢氧化钾 、 18-冠醚-6 、 二异丁基氢化铝 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 132.0h， 生成
  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：

  (S)-2-[(2S,3S)-3-((S)-2-Hydroxy-1-methyl-ethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-propan-1-ol 在 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 bis(acetylacetonate)oxovanadium 、 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 160.75h， 生成 (1R,2R)-1-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-1,3-dihydroxy-2-methylpropyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-2-methylpropane-1,3-diol
  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

文献信息

• Enhancing the binding properties of a conformationally rigid podand ionophore
  作者：Shawn D. Erickson、Michael H.J. Ohlmeyer、W. Clark Still

  DOI：10.1016/s0040-4039(00)61090-0

  日期：1992.9

  Stereospecific functionalization of a conformationally rigid podand yields new ionophores having binding properties comparable to those of the macrocyclic crown ethers.
• A podand analog of 18-crown-6
  作者：Ge Li、W.Clark Still

  DOI：10.1016/s0040-4039(00)77454-5

  日期：1993.2

  Conformationally locked, chiral podands 3 and 4 am prepared and their ionophoric properties are studied. These host molecules have a cation-binding site with six oxygens arranged in the geometry found in the crystal structure of potassium 18-crown-6.
• Enantioselective cation binding with a functionalized podand ionophore
  作者：Alan Armstrong、W. Clark Still

  DOI：10.1021/jo00043a010

  日期：1992.8

  By adding an acetamido group to podand 1, a new ionophore 2 is created which binds peptidic ammonium ions with high enantioselectivity.
• An 18-crown-6 derivative with only one conformation
  作者：Ge Li、W. Clark Still

  DOI：10.1021/ja00062a068

  日期：1993.5
• Two-point binding in podand acetals favors enantioselective complexation.
  作者：Ge Li、W. Clark Still

  DOI：10.1016/s0040-4039(00)61091-2

  日期：1992.9