(2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4,6-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4,6-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4,6-trihydroxyoxane-2-carboxylate
• 化学式: C₁₉H₃₂O₁₆
• 分子量: 516.453
• InChiKey: RMRMXJLCYZJACL-QUFPSSANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  255
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4,6-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4-二甲氨基吡啶 吡啶 作用下， 反应 2.5h， 生成 methyl O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->2)-1,3,4-tri-O-acetyl-α-D-glucopyranuronate
  参考文献：
  名称：

  Synthesis of Neosaponins Carrying Oligosaccharides from Natural Products

  摘要：

  DOI：

  10.3987/com-99-8612
• 作为产物：
  描述：

  大豆皂苷 Bb 在 glycyrrhizinic acid hydrolase 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 18.0h， 生成 (2S,3S,4S,5R)-5-[(2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4,6-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemical transglycosylation of functional bioactive glyco-linkages

  摘要：

  The natural functional bioactive oligosaccharides moieties, mimosatetraose and fabatriose, were cut off from julibrosides and soyasaponin I by chemical and enzymatic methods, respectively, and were pasted to diosgenin to give neosaponins 1 and 2. The obtained neosaponins were tested for cytotoxicity and hepatoprotective activity. This method could be applied to the synthesis of novel bioactive glycosides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00519-x