(E)-(4R,5R)-4-Azido-5,8-dihydroxy-oct-2-enoic acid ethyl ester

• 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: (E)-(4R,5R)-4-Azido-5,8-dihydroxy-oct-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R,5R)-4-azido-5,8-dihydroxyoct-2-enoate
• 化学式: C₁₀H₁₇N₃O₄
• 分子量: 243.263
• InChiKey: QJBAFCVMBCZLNE-JKKBLNIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-(4R,5S)-4-Bromo-5,8-dihydroxy-oct-2-enoic acid ethyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以93%的产率得到(E)-(4R,5R)-4-Azido-5,8-dihydroxy-oct-2-enoic acid ethyl ester
  参考文献：
  名称：

  Regio- and stereoselective ring opening of vinyl epoxides with MgBr2

  摘要：

  The regio- and stereoselective ring opening of vinyl epoxides has been achieved by the use of Lewis acid, MgBr2, affording bromohydrins in excellent yield, which are readily transformed to azidoalcohol, a key intermediate of several classes of pyrrolizidine and indolizidine alkaloids. The scope and limitations of the reaction are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.043

文献信息

• Formal total synthesis of (−)-balanol: a potent PKC inhibitor
  作者：Srinivasarao Yaragorla、Ramaiah Muthyala

  DOI：10.1016/j.tetlet.2009.10.120

  日期：2010.1

  An efficient formal total synthesis of the PKC inhibitor balanol 1 is described, starting from the commercially available pentane1,5-diol. A Shi epoxidation and Pd(0)-mediated nitrogen substitution with double inversion established the correct configuration of the balanol precursor 3.

  描述了一种有效的正式全合成的PKC抑制剂balanol 1，从市售的pentane1,5-diol开始。Shi环氧化和Pd（0）介导的氮取代双转化建立了Balanol前体3的正确构型。
• Regio- and stereoselective ring opening of vinyl epoxides with MgBr2
  作者：Jae Du Ha、Sun Young Kim、Su Jung Lee、Seung Kyu Kang、Jin Hee Ahn、Sung Soo Kim、Joong-Kwon Choi

  DOI：10.1016/j.tetlet.2004.06.043

  日期：2004.7

  The regio- and stereoselective ring opening of vinyl epoxides has been achieved by the use of Lewis acid, MgBr2, affording bromohydrins in excellent yield, which are readily transformed to azidoalcohol, a key intermediate of several classes of pyrrolizidine and indolizidine alkaloids. The scope and limitations of the reaction are discussed. (C) 2004 Elsevier Ltd. All rights reserved.