N-[(6R,8R,9R,10S)-10-Hydroxy-3,5-dioxo-8-((1R,2R)-1,2,3-trihydroxy-propyl)-1,4,7-trioxa-spiro[5.5]undec-9-yl]-acetamide | 471879-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(6R,8R,9R,10S)-10-Hydroxy-3,5-dioxo-8-((1R,2R)-1,2,3-trihydroxy-propyl)-1,4,7-trioxa-spiro[5.5]undec-9-yl]-acetamide
• 英文别名: N-[(6R,8R,9R,10S)-10-hydroxy-3,5-dioxo-8-[(1R,2R)-1,2,3-trihydroxypropyl]-1,4,7-trioxaspiro[5.5]undecan-9-yl]acetamide
• CAS: 471879-24-0
• 化学式: C₁₃H₁₉NO₁₀
• 分子量: 349.295
• InChiKey: OFYRVZPSUBHQPM-DGVFGBESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  苄胺 、 N-[(6R,8R,9R,10S)-10-Hydroxy-3,5-dioxo-8-((1R,2R)-1,2,3-trihydroxy-propyl)-1,4,7-trioxa-spiro[5.5]undec-9-yl]-acetamide 以 N,N-二甲基甲酰胺-d7 为溶剂， 以28 mg的产率得到(2R,4S,5R,6R)-5-Acetylamino-2-(benzylcarbamoyl-methoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-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 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺-d7 、 水 为溶剂， 反应 2.0h， 生成 N-[(6R,8R,9R,10S)-10-Hydroxy-3,5-dioxo-8-((1R,2R)-1,2,3-trihydroxy-propyl)-1,4,7-trioxa-spiro[5.5]undec-9-yl]-acetamide
  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.