ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienylcarboxylate | 1033066-31-7

• 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: ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienylcarboxylate
• 英文别名: ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienoate
• CAS: 1033066-31-7
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: CBRCSGBILOFJNM-OWLPPKTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienylcarboxylate 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and spectroscopic correlation of the diastereoisomers of 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid: implications for the structures of papuamides A–D and mirabamides A–D

  摘要：

  All 4 diastereomeric possibilities for the 2,3-dihydroxy-2,6.8-trimethyldeca-(4Z,6E)-dienoic acid (Dhtda) residue, found in the cyclic depsipeptide natural products papuamides A-D and mirabamides A-D, were stereoselectively synthesized using a Z-selective Wittig reaction of both enantiomers of 2,4-dimethylhex-2-enyl-triphenylphosphonium bromide with all four diastereoisomers; of ethyl-3-formyl-2-methyl-1,4-dioxaspiro[4,4]nonane-2-carboxylate. To elucidate the configuration of Dhtda, the H-1 and C-13 NMR spectra of the synthetic isomers were compared to those of the natural residue. On the basis of that comparison, it is suggested that the likely configuration of the diastereomer present in Dhtda residue is either (2R,3S,8S) or (2S,3R,8S) in the papuamides and mirabimides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.09.031
• 作为产物：
  描述：

  在 ammonium cerium(IV) nitrate 、 borate buffer 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 14.0h， 生成 ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienylcarboxylate
  参考文献：
  名称：

  木瓜酰胺B（一种具有抗HIV特性的有效海洋环二肽）的总合成和结构分配。

  摘要：

  DOI：

  10.1002/anie.200705557

文献信息

• Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties
  作者：Weiqing Xie、Derong Ding、Weiwei Zi、Guangyu Li、Dawei Ma

  DOI：10.1002/anie.200705557

  日期：2008.3.31
• Synthesis and spectroscopic correlation of the diastereoisomers of 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid: implications for the structures of papuamides A–D and mirabamides A–D
  作者：Gurusankar Ramamoorthy、Cristina M. Acevedo、Edgardo Alvira、Mark A. Lipton

  DOI：10.1016/j.tetasy.2008.09.031

  日期：2008.11

  All 4 diastereomeric possibilities for the 2,3-dihydroxy-2,6.8-trimethyldeca-(4Z,6E)-dienoic acid (Dhtda) residue, found in the cyclic depsipeptide natural products papuamides A-D and mirabamides A-D, were stereoselectively synthesized using a Z-selective Wittig reaction of both enantiomers of 2,4-dimethylhex-2-enyl-triphenylphosphonium bromide with all four diastereoisomers; of ethyl-3-formyl-2-methyl-1,4-dioxaspiro[4,4]nonane-2-carboxylate. To elucidate the configuration of Dhtda, the H-1 and C-13 NMR spectra of the synthetic isomers were compared to those of the natural residue. On the basis of that comparison, it is suggested that the likely configuration of the diastereomer present in Dhtda residue is either (2R,3S,8S) or (2S,3R,8S) in the papuamides and mirabimides. (C) 2008 Elsevier Ltd. All rights reserved.