benzyl 3-O-3,4-di-O-benzoyl-β-D-xylopyranosyloleanolate | 1268673-21-7

• 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 3-O-3,4-di-O-benzoyl-β-D-xylopyranosyloleanolate
• 英文别名: benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4R,5R)-4,5-dibenzoyloxy-3-hydroxyoxan-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: 1268673-21-7
• 化学式: C₅₆H₇₀O₉
• 分子量: 887.166
• InChiKey: PGMVDQYPQGJPIN-IGPMUARCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  65
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-3,4-di-O-benzoyl-β-D-xylopyranosyloleanolate 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到benzyl oleanolate 3β-O-[3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,4-di-O-benzoyl-β-D-xylo-pyranoside]
  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：

  齐墩果酸苄酯 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 benzyl 3-O-3,4-di-O-benzoyl-β-D-xylopyranosyloleanolate
  参考文献：
  名称：

  四种具有重要抗肿瘤活性的天然三萜皂苷的简便合成

  摘要：

  通过采用逐步糖基化，首次合成了四种具有显着抗肿瘤活性的天然三萜皂苷。关键中间体 13 是通过 Bu2SnO 介导的区域选择性苯甲酰化得到的。在目标化合物的制备过程中，发现中间体17和20中的α-L-阿拉伯吡喃糖基单元以异常的1 C 4 构象存在，去除苯甲酰基后，α-L-阿拉伯吡喃糖基单元在典型的 4 C 1 形式。

  DOI：

  10.1080/00397910903576602

文献信息

• Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
  作者：Qingchao Liu、Hongchun Liu、Lei Zhang、Tiantian Guo、Peng Wang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.ejmech.2013.04.016

  日期：2013.6

  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.
• Facile Synthesis of Four Natural Triterpene Saponins with Important Antitumor Activity
  作者：Tiantian Guo、Qingchao Liu、Lei Zhang、Peng Wang、Yingxia Li

  DOI：10.1080/00397910903576602

  日期：2011.1.25

  The first synthesis of four natural triterpene saponins, which exhibit significant antitumor activities, was concisely achieved by adopting a stepwise glycosylation. The key intermediate 13 was afforded via Bu2SnO-mediated regioseletive benzoylation. During the preparation of the target compounds, it was found that the α-L-arabinopyranosyl unit in intermediates 17 and 20 existed in the unusual 1 C

  通过采用逐步糖基化，首次合成了四种具有显着抗肿瘤活性的天然三萜皂苷。关键中间体 13 是通过 Bu2SnO 介导的区域选择性苯甲酰化得到的。在目标化合物的制备过程中，发现中间体17和20中的α-L-阿拉伯吡喃糖基单元以异常的1 C 4 构象存在，去除苯甲酰基后，α-L-阿拉伯吡喃糖基单元在典型的 4 C 1 形式。