(3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate | 127761-61-9

• 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: (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-acetyloxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 127761-61-9
• 化学式: C₄₆H₇₂O₁₃
• 分子量: 833.07
• InChiKey: NQKRJRPQGHPXGB-BGCGIHDZSA-N

物化性质

• 沸点：
  768.3±60.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 人参皂甙 Rh2
  参考文献：
  名称：

  Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng

  摘要：

  Condensation of the 12-O-acetylderivative of 20(S)-protopanaxadiol [dammar-24-ene-3 beta,12 beta,20(S)-triol] with tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of silver oxide in dichloroethane, followed by deprotection with sodium methoxide in methanol, results in formation of the 3-O-beta-D-glucopyranosyldammar-24-ene-3 beta,12 beta,20(S)-triol identical with natural ginsenoside-Rh-2. The 12-O-acetyl-20(S)-protopanaxadiol is easily prepared from betulafolienetriol via the 3-keto-12-O-acetylderivative followed by NaBH4 reduction. This comparatively simple five-step synthesis makes this hitherto rare ginsenoside relatively accessible. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00184-5
• 作为产物：
  描述：

  12β,20S-dihydroxydammar-24-en-3-one 在 吡啶 、 sodium tetrahydroborate 、 4 A molecular sieve 、 silver(l) oxide 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 生成 (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate
  参考文献：
  名称：

  Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng

  摘要：

  Condensation of the 12-O-acetylderivative of 20(S)-protopanaxadiol [dammar-24-ene-3 beta,12 beta,20(S)-triol] with tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of silver oxide in dichloroethane, followed by deprotection with sodium methoxide in methanol, results in formation of the 3-O-beta-D-glucopyranosyldammar-24-ene-3 beta,12 beta,20(S)-triol identical with natural ginsenoside-Rh-2. The 12-O-acetyl-20(S)-protopanaxadiol is easily prepared from betulafolienetriol via the 3-keto-12-O-acetylderivative followed by NaBH4 reduction. This comparatively simple five-step synthesis makes this hitherto rare ginsenoside relatively accessible. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00184-5

文献信息

• Synthesis and anti-cancer cell activity of pseudo-ginsenoside Rh2
  作者：Guangtao Qian、Zhicai Wang、Jinyu Zhao、Dandan Li、Wei Gao、Baohui Wang、Dayuan Sui、Xiangru Qu、Yanping Chen

  DOI：10.1016/j.steroids.2014.08.021

  日期：2014.12

  beta-D-Glucopyranoside, (3 beta,12 beta,20E)-12,25-dihydroxydammar-20(22)-en-3-yl (pseudo-ginsenoside Rh2) and its 20Z-isomer were synthesized from ginsenoside Rh2 under a mild condition, via a simple three-step called acetylation, elimination-addition and saponification. In addition, their activities were evaluated by eight different human tumor cells, compared with ginsenoside Rh2 group. Results indicated that the reaction in the side chain might greatly enhance the anti-proliferative activity of ginsenosides. (C) 2014 Elsevier Inc. All rights reserved.