(2S,3R,4S,5R,6R)-2-((2-((3S,5R,8R,9R,10R,13R,14R,17S)-3-acetoxy-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 1309456-08-3

• 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: (2S,3R,4S,5R,6R)-2-((2-((3S,5R,8R,9R,10R,13R,14R,17S)-3-acetoxy-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 1309456-08-3
• 化学式: C₆₆H₇₈O₁₃
• 分子量: 1079.34
• InChiKey: ZRPOLEVCDHOBIW-CSURMCDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.56
• 重原子数：
  79.0
• 可旋转键数：
  16.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  167.03
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-2-((2-((3S,5R,8R,9R,10R,13R,14R,17S)-3-acetoxy-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 吡啶 、 甲醇 、 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3β-acetoxy-12α-hydroxy-20S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)dammar-24-ene
  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：

  3β-acetoxy-20S-hydroxydammar-24-en-12-one 、 perbenzoyl-D-glucopyranosyl o-(1-hexynyl)benzoate 在 Ph₃PAuNTf₂ 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到(2S,3R,4S,5R,6R)-2-((2-((3S,5R,8R,9R,10R,13R,14R,17S)-3-acetoxy-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylhept-5-en-2-yl)oxy)-6-((benzoyloxy)methyl)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