2-epi-jaspine trifluoroacetic acid salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-epi-jaspine trifluoroacetic acid salt
• 英文别名: 2-epi-pachastrissamine trifluoroacetate；2-epi-jaspine B trifluoroacetate；(2R,3S,4S)-4-amino-2-tetradecyloxolan-3-ol;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₁₈H₃₇NO₂
• 分子量: 413.521
• InChiKey: FRCJMCLHTWGJQM-RXQQAGQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-epi-jaspine trifluoroacetic acid salt 以 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到2-acetamido-3-O-acetyl-1,4-anhydro-(2S,3S,4R)-1,3,4-octadecanetriol
  参考文献：
  名称：

  从加纳醛中首次合成脱水植物鞘氨醇pachastrissamine（茉莉花B）

  摘要：

  描述了由加纳的醛合成天然的脱水植物鞘氨醇pachastrissamine（茉莉花B）1a。

  DOI：

  10.1016/j.tetlet.2004.11.035
• 作为产物：
  描述：

  糖脂 在 吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-epi-jaspine trifluoroacetic acid salt
  参考文献：
  名称：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B

  摘要：

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B was achieved by using Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.032

文献信息

• The first synthesis of the anhydrophytosphingosine pachastrissamine (jaspine B) from Garner’s aldehyde
  作者：N. Sudhakar、A. Ravi Kumar、A. Prabhakar、B. Jagadeesh、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2004.11.035

  日期：2005.1

  The synthesis of the natural anhydrophytosphingosine pachastrissamine (jaspine B) 1a from Garner’s aldehyde is described.

  描述了由加纳的醛合成天然的脱水植物鞘氨醇pachastrissamine（茉莉花B）1a。
• Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach
  作者：Gowrisankar Reddipalli、Mallam Venkataiah、Mithilesh Kumar Mishra、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2009.07.004

  日期：2009.8

  2-epi-Jaspine B has been synthesized starting from (-)-diethyl tartrate in 12 simple steps and 26.6% overall yield. The key intermediate was obtained via stereoselective base-catalyzed intramolecular oxy-Michael conjugate addition followed by tandem hydrogenation/hydrogenolysis. (c) 2009 Elsevier Ltd. All rights reserved.
• A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B
  作者：G. Srinivas Rao、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2011.07.032

  日期：2011.9

  A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl D-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B was achieved by using Grignard addition on N-benzyl sugar lactamine and Wittig olefination as key steps. (C) 2011 Elsevier Ltd. All rights reserved.