ethyl (2R,3S)-3-[(1Z,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-methyl-1,4-dioxaspiro[4.4]nonane-2-carboxylate | 1111648-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2R,3S)-3-[(1Z,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-methyl-1,4-dioxaspiro[4.4]nonane-2-carboxylate
• 英文别名: ethyl (2S,3R)-2-[(1Z,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-3-methyl-1,4-dioxaspiro[4.4]nonane-3-carboxylate
• CAS: 1111648-88-4
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: JASCOVUZFTTYKU-IQQBUSDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3S)-3-[(1Z,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-methyl-1,4-dioxaspiro[4.4]nonane-2-carboxylate 在 10-camphorsulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到ethyl (2R,3S,4Z,6E,8S)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienylcarboxylate
  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：

  、 (2E,4S)-2,4-dimethyl-2-hexenyltriphenylphosphonium bromide 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以65%的产率得到ethyl (2R,3S)-3-[(1Z,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-methyl-1,4-dioxaspiro[4.4]nonane-2-carboxylate
  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

文献信息

• 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.