12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one | 127750-93-0

• 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: 12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one
• 英文别名: [(5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-yl] acetate
• CAS: 127750-93-0
• 化学式: C₃₂H₅₂O₄
• 分子量: 500.762
• InChiKey: KVXMPQFKQBICKI-UQVKNAHLSA-N

物化性质

• 沸点：
  568.7±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one 在 sodium tetrahydroborate 、 4 A molecular sieve 、 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 1,2-二氯乙烷 、 异丙醇 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：

  betulafolienetriol 在 吡啶 、 chromium(VI) oxide 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one
  参考文献：
  名称：

  Synthesis of ginsenoside Rg3, a minor constituent of Ginseng Radix

  摘要：

  Glycosylation of 12 beta-acetoxy-dammar-24-en-3 beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha-and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg(3), the minor component of Ginseng Radix rubra. All compounds were fully characterized by H-1 and C-13 NMR spectroscopy, (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)00217-6

文献信息

• Compounds and their preparation for the treatment of Alzheimer's disease by inhibiting beta-amyloid peptide production
  申请人：Landry W. Donald

  公开号：US20060014729A1

  公开（公告）日：2006-01-19

  The present invention provides novel dammarane compounds, compositions (e.g., pharmaceutical compositions) comprising the dammarane compounds, and methods for the synthesis of these dammarane compounds. Additionally, the present invention provides methods for inhibiting beta-amyloid peptide production and methods for treating or preventing a pathological condition, particularly, neurodegeneration diseases (e.g., Alzheimer's disease), using these dammarane compounds.

  本发明提供了新型的丹麦烷化合物、包括药物组合物在内的组合物（例如药物组合物），以及合成这些丹麦烷化合物的方法。此外，本发明还提供了抑制β-淀粉样肽生成的方法以及使用这些丹麦烷化合物治疗或预防病理状况，尤其是神经退行性疾病（例如阿尔茨海默病）的方法。
• Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng
  作者：Lyubov N. Atopkina、Nina I. Uvarova、Georgi B. Elyakov

  DOI：10.1016/s0008-6215(97)00184-5

  日期：1997.10

  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.
• Synthesis of ginsenoside Rg3, a minor constituent of Ginseng Radix
  作者：Victor Ph. Anufriev、Galina V. Malinovskaya、Vladimir A. Denisenko、Nina I. Uvarova、Georgi B. Elyakov、Shin-Il Kim、Nam-In Baek

  DOI：10.1016/s0008-6215(97)00217-6

  日期：1997.11

  Glycosylation of 12 beta-acetoxy-dammar-24-en-3 beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha-and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg(3), the minor component of Ginseng Radix rubra. All compounds were fully characterized by H-1 and C-13 NMR spectroscopy, (C) 1997 Elsevier Science Ltd. All rights reserved.