ginsenoside Rh3 | 166040-90-0

• 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: ginsenoside Rh3
• 英文别名: 3β-O-β-D-glucopyranosyl-5R,9R,13R-dammarane-(E)-20(22),24-(25)-diene-12β-ol；ispginsenoside Rh₃；Isoginsenoside Rh3；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-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]phenanthren-3-yl]oxy]oxane-3,4,5-triol
• CAS: 166040-90-0
• 化学式: C₃₆H₆₀O₇
• 分子量: 604.868
• InChiKey: PHLXREOMFNVWOH-DNQFHFKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以83%的产率得到ginsenoside Rh3
  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