(2R,4S,5R,6R)-5-acetamido-2-(carboxymethoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 37854-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-acetamido-2-(carboxymethoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 37854-54-9
• 化学式: C₁₃H₂₁NO₁₁
• 分子量: 367.31
• InChiKey: DVAGMLRWZHGEIW-DGVFGBESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-5-acetamido-2-(carboxymethoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 在 sodium hydroxide 作用下， 反应 12.0h， 以89%的产率得到(2R,4S,5R,6R)-5-amino-2-(carboxymethoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of O-Glycolyl-Linked Neuraminic Acids through a Spirocyclic Intermediate

  摘要：

  [GRAPHICS]The neuraminic acid derivative 5 is readily converted in several steps to the neuraminic acid dimer 12, linked through the hydroxyl of a 5-N-glycolyl group in an alpha-2,5 glycosidic linkage. The sequence is shown to proceed through a spirocyclic intermediate 9 by in situ NMR experiments. Similar derivatives of N-glycolylneuraminic acid (Neu5Gc), including polymers, have been identified from marine sources, including starfish and sea urchins, often as sulfated derivatives and are thought to mediate sperm-egg recognition.

  DOI：

  10.1021/ol026317g
• 作为产物：
  描述：

  methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-methoxy-2-oxoethoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以93%的产率得到(2R,4S,5R,6R)-5-acetamido-2-(carboxymethoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of O-Glycolyl-Linked Neuraminic Acids through a Spirocyclic Intermediate

  摘要：

  [GRAPHICS]The neuraminic acid derivative 5 is readily converted in several steps to the neuraminic acid dimer 12, linked through the hydroxyl of a 5-N-glycolyl group in an alpha-2,5 glycosidic linkage. The sequence is shown to proceed through a spirocyclic intermediate 9 by in situ NMR experiments. Similar derivatives of N-glycolylneuraminic acid (Neu5Gc), including polymers, have been identified from marine sources, including starfish and sea urchins, often as sulfated derivatives and are thought to mediate sperm-egg recognition.

  DOI：

  10.1021/ol026317g

文献信息

• Synthesis of <i>O</i>-Glycolyl-Linked Neuraminic Acids through a Spirocyclic Intermediate
  作者：Joseph C. McAuliffe、David Rabuka、Ole Hindsgaul

  DOI：10.1021/ol026317g

  日期：2002.9.1

  [GRAPHICS]The neuraminic acid derivative 5 is readily converted in several steps to the neuraminic acid dimer 12, linked through the hydroxyl of a 5-N-glycolyl group in an alpha-2,5 glycosidic linkage. The sequence is shown to proceed through a spirocyclic intermediate 9 by in situ NMR experiments. Similar derivatives of N-glycolylneuraminic acid (Neu5Gc), including polymers, have been identified from marine sources, including starfish and sea urchins, often as sulfated derivatives and are thought to mediate sperm-egg recognition.