3-O-(3,4-di-O-benzoyl-2-O-levulinoyl-β-D-xylopyranosyl)-oleanolic acid 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-glucopyranosyl ester | 1207994-50-0

• 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-(3,4-di-O-benzoyl-2-O-levulinoyl-β-D-xylopyranosyl)-oleanolic acid 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-glucopyranosyl ester
• CAS: 1207994-50-0
• 化学式: C₁₃₅H₁₃₆O₃₄
• 分子量: 2302.54
• InChiKey: WIQUVRRHTDBIBZ-YUGCGBDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.06
• 重原子数：
  169.0
• 可旋转键数：
  36.0
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  423.58
• 氢给体数：
  0.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  3-O-(3,4-di-O-benzoyl-2-O-levulinoyl-β-D-xylopyranosyl)-oleanolic acid 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-glucopyranosyl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 氘代甲醇-d 为溶剂， 反应 5.0h， 以87%的产率得到3-O-β-D-xylopyranosyl 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 and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives

  摘要：

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.016
• 作为产物：
  描述：

  3,4-di-O-benzoyl-2-O-levulinoyl-β-D-xylopyranosyl trichloroacetimidate 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 、 oleanolic acid 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 0.17h， 以65%的产率得到3-O-(3,4-di-O-benzoyl-2-O-levulinoyl-β-D-xylopyranosyl)-oleanolic acid 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-glucopyranosyl ester
  参考文献：
  名称：

  Efficient Synthesis of Flaccidoside II, a Bioactive Component of Chinese Folk Medicine Di Wu

  摘要：

  A bidesmosidic triterpene saponin, flaccidoside II, which was isolated from Di Wu, a Chinese folk medicine from dry rhizome of Anemone flaccida Fr. Schmidt, was efficiently synthesized in a convergent approach. We employed two glycosyl trichloroacetimidate donors in a one-pot reaction as a key step.

  DOI：

  10.1080/07328300903260192