diethyl (2S,3R)-2-methyl-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate | 1149335-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl (2S,3R)-2-methyl-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate
• CAS: 1149335-91-0
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: BSOBMLJGRRGHPW-GWCFXTLKSA-N

物化性质

• 沸点：
  352.2±37.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  diethyl (2S,3R)-2-methyl-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 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：

  diethyl (2S,3S)-2-methyl-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate 在 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 diethyl (2S,3R)-2-methyl-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate
  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