(2S,3R,4S,5R,6R)-2-((allyloxy)carbonyl)-6-(((2R,3R)-3-hydroxy-2-nonadecanamidoicosyl)thio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 1122631-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R,6R)-2-((allyloxy)carbonyl)-6-(((2R,3R)-3-hydroxy-2-nonadecanamidoicosyl)thio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 1122631-77-9
• 化学式: C₆₉H₁₀₃NO₁₁S
• 分子量: 1154.64
• InChiKey: ZBBRHFSDCHCVDI-CWZWUKMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.61
• 重原子数：
  82.0
• 可旋转键数：
  47.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  163.76
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-((allyloxy)carbonyl)-6-(((2R,3R)-3-hydroxy-2-nonadecanamidoicosyl)thio)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 0.25h， 以56%的产率得到(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R)-3-hydroxy-2-(nonadecanoylamino)icosyl]sulfonyloxane-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
• 作为产物：
  描述：

  十九酰氯 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以14 mg的产率得到(2S,3R,4S,5R,6R)-2-((allyloxy)carbonyl)-6-(((2R,3R)-3-hydroxy-2-nonadecanamidoicosyl)thio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  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