(-)-bishomononactic acid | 391198-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (-)-bishomononactic acid
• 英文别名: (2R)-2-[(2R,5S)-5-[(2R)-2-hydroxy-3-methylbutyl]oxolan-2-yl]propanoic acid
• CAS: 391198-93-9
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: CVBMGXOQKKDPQF-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-bishomononactic acid 在 palladium on activated charcoal 咪唑 、 potassium tert-butylate 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (+)-S-2-pyridyl (2S,3S,6R,8S)-[(2'R,3'R,6'S,8'R)-8'-O'-tert-buthydimethylsilylbishomononactoyl]thiobishomononactate
  参考文献：
  名称：

  合成大环内酯α，一种由（+）-和（-）-双糖异酸组成的设计的多乳球蛋白类似物。

  摘要：

  合成了Macrotetrolideα，这是一种由（+）-和（-）-双糖异酸组成的聚乳酸的设计类似物。通过相应的（S）-O-乙酰扁桃酸酯的光学拆分来制备这些单体。单体组装成大四环内酯α进行了七个步骤，而没有任何中间体的损失。

  DOI：

  10.1271/bbb.65.2118
• 作为产物：
  描述：

  (-)-benzyl (2R,3R,6S,8R)-8-O-[(S)-O'-acetylmandeloyl]bishomononactate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以100%的产率得到(-)-bishomononactic acid
  参考文献：
  名称：

  Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

  摘要：

  Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.012

文献信息

• Synthesis of Macrotetrolide α, a Designed Polynactin Analog Composed of (+)- and (−)-Bishomononactic Acids
  作者：Tadaatsu HANADATE、Hiromasa KIYOTA、Takayuki ORITANI

  DOI：10.1271/bbb.65.2118

  日期：2001.1

  Macrotetrolide alpha, a designed analog of polynactin composed of (+)- and (-)-bishomononactic acids, was synthesized. These monomers were prepared via optical resolution of the corresponding (S)-O-acetylmandelates. Assembly of the monomers to macrotetrolide alpha took seven steps without any loss of the intermediates.

  合成了Macrotetrolideα，这是一种由（+）-和（-）-双糖异酸组成的聚乳酸的设计类似物。通过相应的（S）-O-乙酰扁桃酸酯的光学拆分来制备这些单体。单体组装成大四环内酯α进行了七个步骤，而没有任何中间体的损失。
• Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids
  作者：Kentaro Takai、Tadaatsu Hanadate、Masaki Abe、Yukie Ono、Teiko Yamada、Shigefumi Kuwahara、Hiromasa Kiyota

  DOI：10.1016/j.tet.2011.07.012

  日期：2011.9

  Macrotetrolide alpha (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners. (C) 2011 Elsevier Ltd. All rights reserved.