(1R,2R)-1-[(2S,3S,6R,2'S,3'S,6'R)-6'-((1R,2R)-1,5-Dihydroxy-2,5-dimethyl-hexyl)-3,3'-dimethyl-octahydro-[2,2']bipyranyl-6-yl]-2,5-dimethyl-hexane-1,5-diol | 140465-03-8

• 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: (1R,2R)-1-[(2S,3S,6R,2'S,3'S,6'R)-6'-((1R,2R)-1,5-Dihydroxy-2,5-dimethyl-hexyl)-3,3'-dimethyl-octahydro-[2,2']bipyranyl-6-yl]-2,5-dimethyl-hexane-1,5-diol
• 英文别名: (1R,2R)-1-[(2R,5S,6S)-6-[(2S,3S,6R)-6-[(1R,2R)-1,5-dihydroxy-2,5-dimethylhexyl]-3-methyloxan-2-yl]-5-methyloxan-2-yl]-2,5-dimethylhexane-1,5-diol
• CAS: 140465-03-8
• 化学式: C₂₈H₅₄O₆
• 分子量: 486.733
• InChiKey: UOSNUUALQNKTBX-KQAIBFROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-[(2S,3S,6R,2'S,3'S,6'R)-6'-((1R,2R)-1,5-Dihydroxy-2,5-dimethyl-hexyl)-3,3'-dimethyl-octahydro-[2,2']bipyranyl-6-yl]-2,5-dimethyl-hexane-1,5-diol 在 camphor-10-sulfonic acid 作用下， 以 苯 为溶剂， 反应 3.0h， 以96%的产率得到(2R,3R,2'R,5'S,6'S,2''S,3''S,6''R,2'''R,3'''R)-3,6,6,5',3'',3''',6''',6'''-Octamethyl-hexadecahydro-[2,2';6',2'';6'',2''']quaterpyran
  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：

  (2S,3S)-2,3-Bis-((R)-2-iodo-1-methyl-ethyl)-1,4-dioxa-spiro[4.4]nonane 在 盐酸 、 叔丁基过氧化氢 、 三甲基氯硅烷 、 bis(acetylacetonate)oxovanadium 、 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 165.75h， 生成 (1R,2R)-1-[(2S,3S,6R,2'S,3'S,6'R)-6'-((1R,2R)-1,5-Dihydroxy-2,5-dimethyl-hexyl)-3,3'-dimethyl-octahydro-[2,2']bipyranyl-6-yl]-2,5-dimethyl-hexane-1,5-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