(2R,4S,5R,6R)-2-(carboxymethoxy)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 471879-22-8

• 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)-2-(carboxymethoxy)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 471879-22-8
• 化学式: C₂₆H₂₉NO₁₂
• 分子量: 547.516
• InChiKey: HDWIHRNCKPRICP-OPNRPHIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  212
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-2-(carboxymethoxy)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 methyl (2R,4S,5R,6R)-5-[[2-[(2R,4S,5R,6R)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxy-2-methoxycarbonyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxyacetyl]amino]-4-hydroxy-2-(2-methoxy-2-oxoethoxy)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  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 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 14.0h， 生成 (2R,4S,5R,6R)-2-(carboxymethoxy)-5-(9H-fluoren-9-ylmethoxycarbonylamino)-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.