[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-oxo-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate | 1309456-09-4

• 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)-3,4,5-tribenzoyloxy-6-[[(3S,5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-oxo-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate
• CAS: 1309456-09-4
• 化学式: C₉₈H₁₀₂O₂₁
• 分子量: 1615.88
• InChiKey: OHJUYVDTYHCLOD-GEHZSNCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.5
• 重原子数：
  119
• 可旋转键数：
  34
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  264
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-oxo-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate 在 甲醇 、 potassium hydroxide 作用下， 以80%的产率得到3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside
  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 、 3β-hydroxy-20(S)-hydroxydammarane-24-ene-12-one 在 Ph₃PAuNTf₂ 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(3S,5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-oxo-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl benzoate
  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