(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,3R)-3-hydroxy-2-(nonadecanoylamino)icosoxy]oxane-2-carboxylic acid | 1122631-58-6

• 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: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,3R)-3-hydroxy-2-(nonadecanoylamino)icosoxy]oxane-2-carboxylic acid
• CAS: 1122631-58-6
• 化学式: C₄₅H₈₇NO₉
• 分子量: 786.187
• InChiKey: DYNZCXOKFAVYPE-PRHVWZPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  55
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5R,6S)-2-((allyloxy)carbonyl)-6-(((2S,3R)-3-hydroxy-2-nonadecanamidoicosyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 sodium n-propoxide 、 水 、 双氧水 作用下， 以 丙醇 为溶剂， 反应 0.17h， 以36%的产率得到(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,3R)-3-hydroxy-2-(nonadecanoylamino)icosoxy]oxane-2-carboxylic acid
  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.