(2S,3S,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3-hydroxyoctadecan-4-yl benzoate | 1009316-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3-hydroxyoctadecan-4-yl benzoate
• 英文别名: [(2S,3S,4S)-2-azido-1-[tert-butyl(diphenyl)silyl]oxy-3-hydroxyoctadecan-4-yl] benzoate
• CAS: 1009316-59-9
• 化学式: C₄₁H₅₉N₃O₄Si
• 分子量: 686.023
• InChiKey: HDEQHAUVRXRFDM-IGMOWHQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.92
• 重原子数：
  49
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3-hydroxyoctadecan-4-yl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到(2S,3S,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3,4-diol
  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：

  [(S)-2-azido-2-((4S,5R)-2,2-dioxo-5-tetradecyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)ethoxy]-tert-butyldiphenylsilane 、 苯甲酸 在 caesium carbonate 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以92%的产率得到(2S,3S,4S)-2-azido-1-(tert-butyl(diphenyl)silyloxy)-3-hydroxyoctadecan-4-yl benzoate
  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.