20,29-epoxy-3,28-di-O-acetyl-betulin | 166040-85-3

• 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: 20,29-epoxy-3,28-di-O-acetyl-betulin
• 英文别名: betulin 20,29-epoxy-3β,28-diacetate；3,28-di-Oacetyl-20,29-epoxybetulin；(20Ξ)-3β,28-diacetoxy-20,29-epoxy-lupane；(20Ξ)-3β,28-Diacetoxy-20,29-epoxy-lupan；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-(2-methyloxiran-2-yl)-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl acetate
• CAS: 166040-85-3
• 化学式: C₃₄H₅₄O₅
• 分子量: 542.8
• InChiKey: GRQFONTVQVTFAO-OZDDRUJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  20,29-epoxy-3,28-di-O-acetyl-betulin 在 1,4-二氧六环 作用下， 生成 3β,28-diacetoxy-29-oxolupane
  参考文献：
  名称：

  Zur Kenntnis der Triterpene。（63. Mitteilung）。苯妥英酯和乙二醛的氧化

  摘要：

  DOI：

  10.1002/hlca.19420250117
• 作为产物：
  描述：

  白桦脂醇 在 吡啶 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 8.0h， 生成 20,29-epoxy-3,28-di-O-acetyl-betulin
  参考文献：
  名称：

  吡啶甲酸铁（III）诱导的氧化作用以及随后的三萜类衍生物与过氧化氢的重排。

  摘要：

  齐墩果烷三萜1b与单加氧酶的简单模型系统FeIII（PA;吡啶甲酸）3 / H2O2 / MeCN系统（试剂系统A）的反应产生了11个α-羟基衍生物3作为主要产物-氧代衍生物4和12-氧代衍生物6。紫杉烷三萜类化合物2b与试剂系统A的反应仅产生氧化性重排化合物，（20R）-醛8和（20S）-醛9为差向异构体。然后，我们发现吡啶甲酸铁（III）配合物FeIII（PA）3可有效地将三萜类环氧化合物5和7重排为相应的羰基化合物6、8和9，且氢化物发生1,2-移位。

  DOI：

  10.1248/cpb.48.120

文献信息

• Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease
  作者：Peter Šilhár、Sami Alakurtti、Kateřina Čapková、Feng Xiaochuan、Charles B. Shoemaker、Jari Yli-Kauhaluoma、Kim D. Janda

  DOI：10.1016/j.bmcl.2011.02.115

  日期：2011.4

  Botulinum neurotoxins (BoNTs) are the most toxic proteins currently known. Current treatments for botulinum poisoning are all protein based with a limited window of opportunity. Inhibition of the BoNT light chain protease (LC) has emerged as a new therapeutic strategy for the treatment of botulism as it may provide an effective post-exposure remedy. As such, a small library of 40 betulin derivatives was synthesized and screened against the light chain of BoNT serotype A (LC/A); five positive hits (IC50 < 100 mu M) were uncovered. Detailed evaluation of inhibition mechanism of three most active compounds revealed a competitive model, with sub-micromolar K-i value for the best inhibitor (7). Unfortunately, an in vitro cell-based assay did not show any protection of rat cerebellar neurons against BoNT/A intoxication by 7. (C) 2011 Elsevier Ltd. All rights reserved.
• Allylic Hydroxylation Through Acid Catalysed Epoxy Ring Opening of Betulinic Acid Derivatives
  作者：Swapan Pramanick、Suparna Mandal、Sibabrata Mukhopadhyay、Sailen Jha

  DOI：10.1080/00397910500180568

  日期：2005.8.1

  Acid catalysed epoxy ring opening of several lupane type triterpenoids leads to unusual allylic hydroxylation. The reaction involves the formation of epoxide by m-chloroperbenzoic acid followed by the treatment of mineral acid. The simple methodology finds utility to introduce a hydroxyl function at the allylic position in these triterpenoids, which is otherwise quite difficult.
• Colorado potato beetle antifeedants by simple modification of the birch bark triterpene betulin.
  作者：Fu-Yung Huang、Bong Youl Chung、Michael D. Bentley、A. Randall Alford

  DOI：10.1021/jf00057a035

  日期：1995.9

  Oxidation of the 19-side-chain of betulin 3 beta,28-diacetate, a pentacyclic triterpene derived from the readily available birchbark triterpene, betulin, yielded compounds active as antifeedants against larvae of the agricultural insect pest Colorado potato beetle, Leptinotarsa decemlineata. Of the eight compounds investigated, the most active was 30-hydroxy-20-oxo-29-norlup-3 beta,28-diacetate (VI). Acetylation of VI significantly reduced antifeedant activity.
• Lindgren,B.O.; Svahn,C.M., Acta Chemica Scandinavica (1947-1973), 1966, vol. 20, p. 1720 - 1721
  作者：Lindgren,B.O.、Svahn,C.M.

  DOI：——

  日期：——