ethyl (2S,3R)-2,3-dihydroxydodecanoate | 893842-43-8

• 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 (2S,3R)-2,3-dihydroxydodecanoate
• CAS: 893842-43-8
• 化学式: C₁₄H₂₈O₄
• 分子量: 260.374
• InChiKey: SUQKWPHFEIBCTM-OLZOCXBDSA-N

物化性质

• 熔点：
  53.4-55.1 °C
• 沸点：
  375.3±9.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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 (2S,3R)-2,3-dihydroxydodecanoate 在 吡啶 、 ruthenium trichloride 、 sodium tetrahydroborate 、 sodium periodate 、 氯化亚砜 作用下， 以 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (R)-ethyl 3-hydroxydodecanoate
  参考文献：
  名称：

  神经营养肽醛：非鲁胺 B 和简化类似物的固相合成。

  摘要：

  已使用固相和液相合成方法的组合来完成神经营养性脂肽醛非鲁胺 B (2) 的全合成。β-羟基脂肪族尾部是通过环状硫酸盐的区域选择性还原开环制备的，然后与固相树脂偶联。然后在细胞毒性和神经生长因子 (NGF) 诱导试验中检查合成化合物。非鲁胺 B 的简化类似物也显示出活性。

  DOI：

  10.1016/j.bmcl.2006.04.029
• 作为产物：
  描述：

  (2e)-2-十二碳烯酸乙酯 在 甲基磺酰胺 、 AD-mix-β 、 sodium sulfite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.75h， 以81%的产率得到ethyl (2S,3R)-2,3-dihydroxydodecanoate
  参考文献：
  名称：

  Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)

  摘要：

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.015

文献信息

• Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)
  作者：David I. MaGee、Peter J. Silk、Junping Wu、Peter D. Mayo、Krista Ryall

  DOI：10.1016/j.tet.2011.05.015

  日期：2011.7

  The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hubner), as the chiral alkenyl epoxide (6Z)-cis-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both threo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to access both enantiomers. A field study and GC/EAD testing indicated that Z6-cis-9S,10R-epoxy-nonadecene was the sex pheromone of the elm spanworm E. subsignaria (Hubner). (C) 2011 Elsevier Ltd. All rights reserved.
• Neurotrophic peptide aldehydes: Solid phase synthesis of fellutamide B and a simplified analog
  作者：John S. Schneekloth、John L. Sanders、John Hines、Craig M. Crews

  DOI：10.1016/j.bmcl.2006.04.029

  日期：2006.7

  have been used to complete the total synthesis of the neurotrophic lipopeptide aldehyde fellutamide B (2). The beta-hydroxy aliphatic tail was prepared by regioselective reductive opening of a cyclic sulfate, and later coupled to a solid phase resin. The synthetic compound was then examined in cytotoxicity and nerve growth factor (NGF) induction assays. A simplified analog of fellutamide B also showed

  已使用固相和液相合成方法的组合来完成神经营养性脂肽醛非鲁胺 B (2) 的全合成。β-羟基脂肪族尾部是通过环状硫酸盐的区域选择性还原开环制备的，然后与固相树脂偶联。然后在细胞毒性和神经生长因子 (NGF) 诱导试验中检查合成化合物。非鲁胺 B 的简化类似物也显示出活性。