benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside | 1021524-64-0

• 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: benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside
• 英文别名: benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-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: 1021524-64-0
• 化学式: C₁₀₃H₁₁₀O₂₃
• 分子量: 1715.99
• InChiKey: WQDAAUJHSRVXDL-OEDPJDAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.2
• 重原子数：
  126
• 可旋转键数：
  32
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  286
• 氢给体数：
  1
• 氢受体数：
  23

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)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4-hydroxy-5-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-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-carboxylic acid
  参考文献：
  名称：

  Facile synthesis and cytotoxicity of triterpenoid saponins bearing a unique disaccharide moiety: hederacolchiside A1 and its analogues

  摘要：

  An improved synthetic approach toward hederacolchiside A(1), an antitumor triterpenoid saponin bearing a unique disaccharide moiety, was established. This approach began from a partially protected intermediate and avoided tedious protection-deprotection manipulation. An abnormal ring conformation ((1)C(4)) of the center arabinose residue was found in the intermediate, which may account for the unusual regioselectivity between 3-OH and 4-OH of arabinose. Two analogues of hederacolchiside A(1) were then facilely prepared by this approach and exhibited significant cytotoxicity in preliminary in vitro assay. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.014
• 作为产物：
  描述：

  benzyl 3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl)-oleanolate 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以65%的产率得到benzyl oleanolate 3-O-2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranoside
  参考文献：
  名称：

  Facile synthesis and cytotoxicity of triterpenoid saponins bearing a unique disaccharide moiety: hederacolchiside A1 and its analogues

  摘要：

  An improved synthetic approach toward hederacolchiside A(1), an antitumor triterpenoid saponin bearing a unique disaccharide moiety, was established. This approach began from a partially protected intermediate and avoided tedious protection-deprotection manipulation. An abnormal ring conformation ((1)C(4)) of the center arabinose residue was found in the intermediate, which may account for the unusual regioselectivity between 3-OH and 4-OH of arabinose. Two analogues of hederacolchiside A(1) were then facilely prepared by this approach and exhibited significant cytotoxicity in preliminary in vitro assay. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.014