(2S,3R,4S)-2-azidooctadecane-1,3,4-triol

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S,3R,4S)-2-azidooctadecane-1,3,4-triol
• 化学式: C₁₈H₃₇N₃O₃
• 分子量: 343.51
• InChiKey: MUTDVCKHIMUXFS-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-2-azidooctadecane-1,3,4-triol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到DL-arabino-2-Amino-1,3,4-trihydroxy-octadecan
  参考文献：
  名称：

  Efficient and Selective Synthesis of d-arabino-, d-lyxo-, and d-xylo-Phytosphingosine from d-ribo-Phytosphingosine

  摘要：

  A new high-yield approach to the regio- and stereoselective synthesis Of D-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.

  DOI：

  10.1021/jo702147y
• 作为产物：
  描述：

  (2S,3R,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3,4-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到(2S,3R,4S)-2-azidooctadecane-1,3,4-triol
  参考文献：
  名称：

  Efficient and Selective Synthesis of d-arabino-, d-lyxo-, and d-xylo-Phytosphingosine from d-ribo-Phytosphingosine

  摘要：

  A new high-yield approach to the regio- and stereoselective synthesis Of D-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.

  DOI：

  10.1021/jo702147y

文献信息

• Efficient and Selective Synthesis of <scp>d</scp>-<i>arabino</i>-, <scp>d</scp>-<i>lyxo</i>-, and <scp>d</scp>-<i>xylo</i>-Phytosphingosine from <scp>d</scp>-<i>ribo</i>-Phytosphingosine
  作者：Sanghee Kim、Nakyong Lee、Sukjin Lee、Taeho Lee、Yun Mi Lee

  DOI：10.1021/jo702147y

  日期：2008.2.1

  A new high-yield approach to the regio- and stereoselective synthesis Of D-arabino-, D-lyxo-, and D-xylo-phytosphingosines from inexpensive D-ribo-phytosphingosine is described. The synthetic methodologies mainly rely on the selective configurational inversion of the stereocenter through a neighboring group participation mechanism.