(2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethyl-12-(pivaloyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 873850-51-2

• 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: (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethyl-12-(pivaloyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 873850-51-2
• 化学式: C₆₉H₈₆O₁₃
• 分子量: 1123.43
• InChiKey: ISGLHZKMWYUQFK-DSMPEAFMSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.38
• 重原子数：
  82.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  170.19
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethyl-12-(pivaloyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 甲醇 、 potassium hydroxide 作用下， 以76%的产率得到人参皂甙 Rh2
  参考文献：
  名称：

  Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor

  摘要：

  Glycosylation of the acid labile protopanaxadiol derivatives was succeeded with a glycosyl ortho-hexynylbenzoate as donor under the catalysis of PPh(3)AuNTf(2), leading to the subsequent elaboration of ginsenoside Rh2 and chikusetsusaponin-LT8 in a concise manner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.003
• 作为产物：
  描述：

  perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 、 12-pivaloyl-protopanaxdiol 在 Ph₃PAuNTf₂ 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-(2-hydroxy-6-methylhept-5-en-2-yl)-4,4,8,10,14-pentamethyl-12-(pivaloyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor

  摘要：

  Glycosylation of the acid labile protopanaxadiol derivatives was succeeded with a glycosyl ortho-hexynylbenzoate as donor under the catalysis of PPh(3)AuNTf(2), leading to the subsequent elaboration of ginsenoside Rh2 and chikusetsusaponin-LT8 in a concise manner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.003