benzyl (2S,3S,6R,8S)-3,6-epoxy-2,9-dimethyl-8-hydro-xydecanoate | 391198-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2S,3S,6R,8S)-3,6-epoxy-2,9-dimethyl-8-hydro-xydecanoate
• 英文别名: benzyl (2S)-2-[(2S,5R)-5-[(2S)-2-hydroxy-3-methylbutyl]oxolan-2-yl]propanoate
• CAS: 391198-92-8
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: KQWIRCAREURNEX-RANZSIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S,6R,8S)-3,6-epoxy-2,9-dimethyl-8-hydro-xydecanoate 在 palladium on activated charcoal 氢气 、 silver perchlorate 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 (+)-benzyl (2S,3S,6R,8S)-8-O-((2'R,3'R,6'S,8'R)-8'-O'-{(2S,3S,6R,8S)-8-O-[(2R,3R,6S,8R)-8-O-tert-butyldimethylsilylbishomononactoyl]bishomononactoyl}bisho-mononactoyl)bishomononactate
  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：

  (+/-)-methyl bishomononactate 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 benzyl (2S,3S,6R,8S)-3,6-epoxy-2,9-dimethyl-8-hydro-xydecanoate
  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.