2,3-di-epi-20-hydroxyecdysone 20,22-acetonide | 698975-67-6

• 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: 2,3-di-epi-20-hydroxyecdysone 20,22-acetonide
• 英文别名: (2R,3S,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 698975-67-6
• 化学式: C₃₀H₄₈O₇
• 分子量: 520.707
• InChiKey: GXNNYSDWRVKVJY-XSVXXXMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-di-epi-20-hydroxyecdysone 20,22-acetonide 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以80%的产率得到2,3-diepi-5α-20-hydroxyecdysone 20,22-acetonide
  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
• 作为产物：
  描述：

  蜕皮激素 在 吡啶 、 dihydroquinidine 1,4-phthalazinediyl diether 、 四氧化锇 、 水 、 对甲苯磺酸 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 72.0h， 生成 2,3-di-epi-20-hydroxyecdysone 20,22-acetonide
  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

• A short way to invert configuration of the 2,3-hydroxy groups in ecdysteroids
  作者：R. G. Savchenko、S. A. Kostyleva、V. V. Kachala、L. M. Khalilov、V. N. Odinokov

  DOI：10.1134/s1070428013070063

  日期：2013.7

  3-epi-2-Dehydro-20-hydroxyecdysone and its 20,22-acetonide were reduced with lithium tris(secbutyl) hydridoborate selectively at the 2-oxo group with formation of 2 beta,3 beta-dihydroxy derivatives and the corresponding 2 alpha,3 alpha epimers which were separated by chromatography.
• Stereoselective synthesis and moulting activity of 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5α-20-hydroxyecdysone
  作者：Sureeporn Homvisasevongsa、Aporn Chuaynugul、Nitirat Chimnoi、Apichart Suksamrarn

  DOI：10.1016/j.tet.2004.02.042

  日期：2004.4

  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.