(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid | 81053-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
• 英文别名: 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside oleanolic acid
• CAS: 81053-27-2
• 化学式: C₄₄H₆₇NO₁₁
• 分子量: 786.016
• InChiKey: MZTOVHKIDZXSCI-IOSIUUOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  56.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  163.76
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3β)-3-{[2-(乙酰基氨基)-2-脱氧-β-D-吡喃葡萄糖基]氧代}齐墩果-12-烯-28-酸
  参考文献：
  名称：

  Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins

  摘要：

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2010.01.002
• 作为产物：
  描述：

  28-O-benzyl-3-O-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]oleanolic ester 在 palladium 10% on activated carbon 、 氢气 作用下， 反应 4.0h， 以90%的产率得到(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
  参考文献：
  名称：

  从金合欢根中分离的天然齐墩果酸双糖苷皂苷，albidoside A 的全合成和抗癌活性

  摘要：

  首次合成含有 N-乙酰葡糖胺的天然三萜皂苷，从白相思根中分离出来的白糖苷 A，是在收敛策略中简明地实现的。初步药理研究显示对 HL-60、MCF-7、MDA-MB-231、Hep-2 和 Hela 细胞系具有抗癌活性。特别是，它表现出良好的选择性，对 Hep-2 细胞的细胞毒性 (IC50 = 8.91 μM) 是 Hela 细胞系的五倍。

  DOI：

  10.1177/1747519819884152