5R,9R,13R-dammarane-(E)-20(22),24(25)-diene-3β,12β-diol

• 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: 5R,9R,13R-dammarane-(E)-20(22),24(25)-diene-3β,12β-diol
• 英文别名: (3S,5R,8R,9R,10R,12R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2E)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: OURRZLJECNEIMI-PHSJGONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5R,9R,13R-dammarane-(E)-20(22),24(25)-diene-3β,12β-diol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以54%的产率得到
  参考文献：
  名称：

  Synthesis of Δ²⁰-Ginsenosides Rh₄, (20E)-Rh₃, Rg₆, and Rk₁: A General Approach To Access Dehydrated Ginsenosides

  摘要：

  Four representative Delta(20)-ginsenosides, namely, ginsenosides Rh-4 (1), (20E)-Rh-3 (2), Rg(6) (3), and Rk(1) (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Delta(20)-sapogenins, which were separated due to a judicious choice of protecting groups. The Delta(20)-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Delta(20,21) double bond from isomerization.

  DOI：

  10.1021/acs.joc.7b02987
• 作为产物：
  描述：

  原人参二醇 在 吡啶 、 三氯氧磷 作用下， 反应 4.0h， 生成 5R,9R,13R-dammarane-(E)-20(22),24(25)-diene-3β,12β-diol
  参考文献：
  名称：

  Synthesis of Δ²⁰-Ginsenosides Rh₄, (20E)-Rh₃, Rg₆, and Rk₁: A General Approach To Access Dehydrated Ginsenosides

  摘要：

  Four representative Delta(20)-ginsenosides, namely, ginsenosides Rh-4 (1), (20E)-Rh-3 (2), Rg(6) (3), and Rk(1) (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Delta(20)-sapogenins, which were separated due to a judicious choice of protecting groups. The Delta(20)-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Delta(20,21) double bond from isomerization.

  DOI：

  10.1021/acs.joc.7b02987

文献信息

• Synthesis of Δ²⁰-Ginsenosides Rh₄, (20<i>E</i>)-Rh₃, Rg₆, and R<i>k</i>₁: A General Approach To Access Dehydrated Ginsenosides
  作者：Renzeng Shen、Stephane Laval、Xin Cao、Biao Yu

  DOI：10.1021/acs.joc.7b02987

  日期：2018.3.2

  Four representative Delta(20)-ginsenosides, namely, ginsenosides Rh-4 (1), (20E)-Rh-3 (2), Rg(6) (3), and Rk(1) (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Delta(20)-sapogenins, which were separated due to a judicious choice of protecting groups. The Delta(20)-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of Ph3PAuNTf2 as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Delta(20,21) double bond from isomerization.