oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester | 676530-80-6

• 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: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
• 英文别名: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl oleanate；[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-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: 676530-80-6
• 化学式: C₆₄H₇₄O₁₂
• 分子量: 1035.28
• InChiKey: OZBWYFRVWBBXIS-YTKSOPKMSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  76
• 可旋转键数：
  16
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到齐墩果酸 beta-D-吡喃葡萄糖基酯
  参考文献：
  名称：

  一系列作为α-葡萄糖苷酶和α-淀粉酶抑制剂的齐墩果酸皂苷的合成与评价

  摘要：

  以一种有效且实用的策略合成了 16 种天然存在的齐墩果酸皂苷及其衍生物，并在体外评估了它们对 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。在所有化合物中，28-O-单糖苷 8 对 α-葡萄糖苷酶表现出显着的抑制活性，IC50 值为 87.3 µM，是抗糖尿病阿卡波糖的 5 倍。根据初步的构效关系，对于 28-O-单糖苷，末端 α-l-吡喃鼠李糖残基的存在增强了 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。此外，对于 3,28-O-bidesmosides，

  DOI：

  10.1002/ardp.201500179
• 作为产物：
  描述：

  perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 、 齐墩果酸 在 trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
  参考文献：
  名称：

  Chemoselective glycosylation of carboxylic acid with glycosyl ortho-hexynylbenzoates as donors

  摘要：

  The gold(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3 center dot Et2O and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive instead, orthoester formation with the alcohol was effected selectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.039

文献信息

• Stereocontrolled synthesis of oleanolic saponin ladyginoside A isolated from Ladyginia bucharica
  作者：Matylda Stefaniak、Grzegorz Łopatkiewicz、Magdalena Antkowiak、Jacek Mlynarski

  DOI：10.1016/j.carres.2018.01.011

  日期：2018.3

  Efficient stereocontrolled synthesis of ladyginoside A isolated from Ladyginia bucharica is described. The presented methodology bases on the β-selective glycosylation to construct oleanate-3-O-β-glycoside from selectively protected d-cellobiose comprising desired β-linkage in carbohydrate unit. By using this procedure, dimethyl ester of ladyginoside A (1) (methyl oleanate 3-O-(β-d-glucopyranosyl)

  描述了一种有效的立体控制的瓢虫苷A的合成，该瓢虫苷是从瓢虫中分离得到的。所提出的方法基于β-选择性糖基化，以由在碳水化合物单元中包含所需β-键的选择性保护的d-纤维二糖构建齐墩果酸酯-3-O-β-糖苷。通过该方法，以总收率16％得到了瓢虫苷A（1）的二甲酯（齐墩果酸3-O-（β-d-吡喃葡萄糖基）-（1→4）-β-d-葡糖醛酸甲酯）。在合成具有附加葡萄糖单元的皂苷2的过程中，精细合成也被证明是有用的方法，即3-O- [β-d-吡喃葡萄糖基-（1→4）-β-d-葡萄糖醛酸]齐墩果酸28-O-β- d-吡喃葡萄糖基酯。
• Facile Synthesis of Ginsenoside Ro
  作者：Biao Yu、Wenjie Peng、Jiansong Sun、Feng Lin、Xiuwen Han

  DOI：10.1055/s-2003-44985

  日期：——

  Two concise synthetic routes, being different in the glycosylation sequence, toward ginsenoside Ro (1) are developed. These syntheses feature the elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation and the installation of AZMB as a benzoylic neighboring participating group capable of being selectively removed afterward.

  我们开发了两条简明的合成路线，它们在糖基化顺序上有所不同，最终都导向人参皂苷 Ro (1)。这些合成路线的特点是，在后期通过 TEMPO 介导的选择性氧化来处理葡萄糖醛酸残基，并引入 AZMB 作为邻苯甲酰基参与基团，以便日后选择性去除。
• Synthesis of a Typical Glucuronide-Containing Saponin, 28-<i>O</i>-β-<scp>d</scp>-Glucopyranosyl Oleanate 3-<i>O</i>-β-<scp>d</scp>-Galactopyranosyl-(1→2)-[β-<scp>d</scp>-glucopyranosyl-(1→3)]-β-<scp>d</scp>-glucuronopyranoside
  作者：Biao Yu、Wenjie Peng、Xiuwen Han

  DOI：10.1055/s-2004-829103

  日期：——

  28-O-β-d-Glucopyranosyl oleanate 3-O-β-d-galactopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucuronopyranoside (1), a structurally typical glucuronide-containing triterpene saponin isolated from Aralia dasyphylla, was concisely synthesized in linear nine steps and 26% overall yield. The key features of the synthesis are: (1) attachment of the 28-glucosyl ester ahead of assembly of the 3-O-sugar chain; (2) elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation; (3) installation of 2-(azidomethyl)benzoyl group as a benzoylic neighboring participating group which is selectively removed afterwards for synthesis of the 1→2 sugar linkage.

  28-O-β-d-Glucopyranosyl oleanate 3-O-β-d-galactopyranosyl-(1→2)-[δ-d-glucopyranosyl-(1→3)]-δ-d-glucuronopyranoside (1)是从旱金莲中分离出来的一种结构上典型的含葡糖醛酸的三萜皂甙，该化合物通过 9 个步骤线性合成，总收率为 26%。合成的主要特点是(1) 在组装 3-O 糖链之前连接 28-葡萄糖基酯；(2) 在后期通过 TEMPO 介导的选择性氧化作用详细说明葡萄糖醛酸残基；(3) 安装 2-（叠氮甲基）苯甲酰基作为苯甲酰基邻接参与基团，之后选择性地去除该基团以合成 1→2 糖链。
• Synthesis of Betavulgaroside III, a Representative Triterpene <i>seco</i>-Glycoside
  作者：Shilei Zhu、Yingxia Li、Biao Yu

  DOI：10.1021/jo800669h

  日期：2008.7.1

  Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2 ''-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.
• Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents
  作者：Jun-Feng Li、Song-Jie Chen、Yu Zhao、Jian-Xin Li

  DOI：10.1016/j.carres.2009.01.019

  日期：2009.3

  Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including D-galactopyranosides, D-glucopyranosides, D-xylopyranoses, D-arabopyranoses and D-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1 alpha,25-dihydroxyvitamin D-3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed. (C) 2009 Elsevier Ltd. All rights reserved.