(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-amino-2-(3-azidopropoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid | 1158797-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-amino-2-(3-azidopropoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
• CAS: 1158797-13-7
• 化学式: C₄₅H₇₅N₇O₃₅
• 分子量: 1274.12
• InChiKey: SQHPGCDYVSCWIL-OVHFKZJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -19.1
• 重原子数：
  87
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  663
• 氢给体数：
  22
• 氢受体数：
  41

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-amino-2-(3-azidopropoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid 、 乙酸酐 在 lithium hydroxide 、 水 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2-(3-azidopropoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713
• 作为产物：
  描述：

  在 氢氧化钾 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 106.0h， 以64 mg的产率得到(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-amino-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-amino-2-(3-azidopropoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies

  摘要：

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.

  DOI：

  10.1021/jo9003713