3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl] ester | 1173891-82-1

• 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: 3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl] ester
• CAS: 1173891-82-1
• 化学式: C₁₁₃H₁₂₆O₃₃
• 分子量: 2012.22
• InChiKey: YONWWNOOQDRAKS-OGDYWTSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.93
• 重原子数：
  146.0
• 可旋转键数：
  29.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  406.51
• 氢给体数：
  0.0
• 氢受体数：
  33.0

反应信息

• 作为反应物：
  描述：

  3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl] ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以85%的产率得到3-O-[α-L-rhamnopyranosyl]oleanolic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl] ester
  参考文献：
  名称：

  Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu

  摘要：

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.04.005
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 、 3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-trityl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到3-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl]oleanolic acid 28-O-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzoyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl] ester
  参考文献：
  名称：

  Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu

  摘要：

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.04.005