benzyl (4aS,6aS,6bR,8aR,11R,12aR,12bR,14bS)-11-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate | 876724-30-0

• 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 (4aS,6aS,6bR,8aR,11R,12aR,12bR,14bS)-11-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
• 英文别名: benzyl (4aS,6aR,6aS,6bR,8aR,11R,12aR,14bS)-11-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 876724-30-0
• 化学式: C₃₉H₅₄O₅
• 分子量: 602.855
• InChiKey: KTZGKERIFAEKAW-RLKFXKHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (4aS,6aS,6bR,8aR,11R,12aR,12bR,14bS)-11-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 在 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以78%的产率得到2α-acetyloxy-3β-hydroxyolean-12-en-28-oic acid benzyl ester
  参考文献：
  名称：

  Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum

  摘要：

  Stryphnoside A, alpha-L-rhamnopyranosyl 3 beta-O-[alpha-L-arabinopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucopyranosyl]-2 alpha-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2 alpha, 3 beta-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC50 at mM level. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.006
• 作为产物：
  描述：

  齐墩果酸 在 吡啶 、 硫酸 、 potassium carbonate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl (4aS,6aS,6bR,8aR,11R,12aR,12bR,14bS)-11-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
  参考文献：
  名称：

  五环三萜。第2部分：作为糖原磷酸化酶抑制剂的山楂酸衍生物的合成和生物学评估。

  摘要：

  描述了一系列山楂酸衍生物的合成，并评估了它们对兔肌肉糖原磷酸化酶的作用。在这一系列化合物中，15（IC（50）= 7 microM）是最有效的GPa抑制剂。讨论了山梨酸衍生物的SAR。

  DOI：

  10.1016/j.bmcl.2005.10.014

文献信息

• Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors
  作者：Xiaoan Wen、Pu Zhang、Jun Liu、Luyong Zhang、Xiaoming Wu、Peizhou Ni、Hongbin Sun

  DOI：10.1016/j.bmcl.2005.10.014

  日期：2006.2

  The synthesis of a series of maslinic acid derivatives is described and their effect on rabbit muscle glycogen phosphorylase a evaluated. Within this series of compounds, 15 (IC(50)=7 microM) is the most potent GPa inhibitor. SAR of the maslinic acid derivatives are discussed.

  描述了一系列山楂酸衍生物的合成，并评估了它们对兔肌肉糖原磷酸化酶的作用。在这一系列化合物中，15（IC（50）= 7 microM）是最有效的GPa抑制剂。讨论了山梨酸衍生物的SAR。
• Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum
  作者：Xun Lv、Shouyi Yu、Jing Wang、Yuguo Du

  DOI：10.1016/j.carres.2011.06.006

  日期：2011.9

  Stryphnoside A, alpha-L-rhamnopyranosyl 3 beta-O-[alpha-L-arabinopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 2)-beta-D-glucopyranosyl]-2 alpha-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2 alpha, 3 beta-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC50 at mM level. (C) 2011 Elsevier Ltd. All rights reserved.