20-hydroxyecdysone 20,22-acetonide 2,3-dimesylate | 698975-65-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 20-hydroxyecdysone 20,22-acetonide 2,3-dimesylate
• 英文别名: 20-hydroxyecdysone-20,22-acetonide-2,3-dimesylate
• CAS: 698975-65-4
• 化学式: C₃₂H₅₂O₁₁S₂
• 分子量: 676.89
• InChiKey: UBHNRXSSRLUULG-IBVQXDPUSA-N

物化性质

• 沸点：
  799.9±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  162.73
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  20-hydroxyecdysone 20,22-acetonide 2,3-dimesylate 在 苄基三甲基氯化铵 吡啶 、 四氧化锇 、 溶剂黄146 、 sodium iodide 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 蜕皮激素
  参考文献：
  名称：

  [EN] ECDYSTEROID ANALOGUES HAVING PLANT GROWTH PROMOTING ACTIVITY
  [FR] ANALOGUES D'ECDYSTÉROÏDES AYANT UNE ACTIVITÉ FAVORISANT LA CROISSANCE VÉGÉTALE

  摘要：

  公开号：

  WO2012053994A3
• 作为产物：
  描述：

  蜕皮激素 在 吡啶 、 对甲苯磺酸 作用下， 生成 20-hydroxyecdysone 20,22-acetonide 2,3-dimesylate
  参考文献：
  名称：

  Stereoselective synthesis and moulting activity of 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5α-20-hydroxyecdysone

  摘要：

  The ecdysteroid analogues 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5alpha-20-hydroxyecdysone have been synthesized from the readily available ecdysteroid, 20-hydroxyecdysone, and moulting activity has been determined using the Musca bioassay. As expected, the 2,3-diepi-analogue was less active than the parent ecdysteroid, 20-hydroxyecdysone. However, the 2,3-diepi-5alpha-analogue, which was expected to be inactive in the assay, exhibited moulting activity though it was approximately 1.5-fold less active than its 5beta-analogue. The activity of the 5alpha-analogue could possibly result from the ability of this compound to bind to the ecdysteroid receptor. Alternatively, a possible in vivo C-5 epimerization of the 2,3-diepi-5alpha-analogue to the corresponding 5beta-analogue could account for its activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.042

文献信息

• Sonochemically assisted 2,3-dideoxygenation and skeletal rearrangement of ecdysteroid derivatives
  作者：Rimma G. Savchenko、Svetlana A. Kostyleva、Anastasiya V. Apaeva、Eketerina S. Mesheryakova、Adis A. Tukhbatullin、Victor N. Odinokov、Lyudmila V. Parfenova

  DOI：10.1016/j.ultsonch.2018.12.029

  日期：2019.4

  Sonochemical 2,3- dideoxygenation of ecdysteroids with the Δ 2(3)- bond generation and activation of the C-C bonds of the steroid core in the poststerone derivatives, that causes the skeletal rearrangement have been carried out for the first time. Thus, the ultrasonically assisted reaction of 2,3-dimesyloxy derivatives of ecdysteroids with the NaI-Zn-DMF system gives rise to their 2,3-dideoxy- Δ 2(3)-analogues

  蜕皮类固醇的声化学2，3-双脱氧与poststerone衍生物中的类固醇核的Δ2 （3）键生成和CC键活化激活，这是首次引起骨骼重排。因此，蜕皮类固醇的2，3-二甲磺酰氧基衍生物与NaI-Zn-DMF系统的超声辅助反应产生了它们的2，3-二脱氧-Δ2 （3） -类似物，产率为70-92％。在以2,3-二甲基二氧基氧固酮作为初始蜕皮甾类底物的情况下，反应伴随着烯丙基部分的活化和半频哪醇重排，从而导致C 13 -C 14通过C / D环的收缩/扩展键迁移，并提供了新颖的短链（8 R）-13（14→8）-abeo-异构体。
• Deoxygenation of Ecdysteroid Mesylates by Sonication
  作者：R. G. Savchenko、R. M. Limantseva、V. N. Odinokov

  DOI：10.1007/s10600-023-03927-7

  日期：——

  New Δ2,3-steroids that were practicable promising precursors of natural steroidal compounds were synthesized by targeted sonochemical deoxygenation of ecdysteroid mesylates that were derivatives of 20-hydroxyecdysone. The structures of the synthesized compounds and the configuration of the atoms were established using 1D and 2D 1H NMR and 13C NMR. The empirical compositions were confirmed by measuring their masses using HR-MS.

  通过对作为 20-hydroxyecdysone 衍生物的蜕皮激素甲磺酸盐进行有针对性的超声化学脱氧合成了新的Δ2,3-类固醇，它们是天然类固醇化合物的有前途的前体。利用一维和二维 1H NMR 和 13C NMR 确定了合成化合物的结构和原子构型。利用 HR-MS 测量了这些化合物的质量，从而确认了它们的经验组成。