prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2S,3R)-2-azido-3-phenylmethoxyicosoxy]-3,4,5-tribenzoyloxyoxane-2-carboxylate | 1122631-53-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2S,3R)-2-azido-3-phenylmethoxyicosoxy]-3,4,5-tribenzoyloxyoxane-2-carboxylate
• CAS: 1122631-53-1
• 化学式: C₅₇H₇₁N₃O₁₁
• 分子量: 974.204
• InChiKey: MNSGPCGYZVXRCE-WPFJAJKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  71
• 可旋转键数：
  37
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2S,3R)-2-azido-3-phenylmethoxyicosoxy]-3,4,5-tribenzoyloxyoxane-2-carboxylate 在 四氯化钛 、 水 、 碳酸氢钠 作用下， 以 氯仿 、 乙醚 为溶剂， 反应 3.5h， 以83%的产率得到prop-2-enyl (2S,3S,4S,5R,6S)-6-[(2S,3R)-2-azido-3-hydroxyicosoxy]-3,4,5-tribenzoyloxyoxane-2-carboxylate
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h
• 作为产物：
  描述：

  (2S,3R)-2-azido-3-(benzyloxy)icosan-1-ol 、 prop-2-enyl (2S,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxane-2-carboxylate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以96%的产率得到prop-2-enyl (2S,3S,4S,5R,6R)-6-[(2S,3R)-2-azido-3-phenylmethoxyicosoxy]-3,4,5-tribenzoyloxyoxane-2-carboxylate
  参考文献：
  名称：

  α-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives

  摘要：

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.

  DOI：

  10.1021/ol802915h

文献信息

• α-Glycosphingolipids via Chelation-Induced Anomerization of <i>O</i>- and <i>S</i>-Glucuronic and Galacturonic Acid Derivatives
  作者：Wayne Pilgrim、Paul V. Murphy

  DOI：10.1021/ol802915h

  日期：2009.2.19

  Bacterial glycolipids containing either alpha-glucuronic acid or alpha-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel alpha-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of alpha) were observed from O-glycoside precursors.