methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-methoxy-2-oxoethoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 471879-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-methoxy-2-oxoethoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 471879-19-3
• 化学式: C₂₃H₃₃NO₁₅
• 分子量: 563.513
• InChiKey: CDROIERGIFBGEU-GYXCGWDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  205.36
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  羟乙酸甲酯 、 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 silver zeolite 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-methoxy-2-oxoethoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]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