benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4-O-acetyl-α-L-arabinopyranoside | 875878-29-8

• 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: benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4-O-acetyl-α-L-arabinopyranoside
• 英文别名: benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-acetyloxy-4-hydroxy-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 875878-29-8
• 化学式: C₇₁H₈₆O₁₅
• 分子量: 1179.45
• InChiKey: XSCVDUCTEQEHIS-VDZPILEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  86
• 可旋转键数：
  19
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4-O-acetyl-α-L-arabinopyranoside 在 乙酰氯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 生成 benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3-O-benzoyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of β-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety

  摘要：

  A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach P-hederin (oleanolic acid 3-0-Gt-L-rhamnopyranosyl-(1 -> 2)-alpha- L-arabinopyrano side) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A, (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2005.10.015
• 作为产物：
  描述：

  benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-4-O-acetyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis of β-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety

  摘要：

  A facile synthetic approach toward oleanolic acid glycoside bearing alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl moiety, a unique oligosaccharide that strongly induces antitumor activity of oleanane-type triterpenoid saponins, was developed. Based on this approach P-hederin (oleanolic acid 3-0-Gt-L-rhamnopyranosyl-(1 -> 2)-alpha- L-arabinopyrano side) was efficiently prepared from oleanolic acid through stepwise glycosylation in linear eight steps with 52% overall yield, while Hederacolchiside A, (oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-[beta-D-glucopyranosyl-(1 -> 4)]-alpha-L-arabinopyranoside) in linear 13 steps with 20% overall yield. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2005.10.015