(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol | 91708-76-8

• 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: (2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol
• 英文别名: (2S,3R,4R,5S)-5,6-dimethyl-2-[(1'S,2'R,4'R,8'S,10'S,13'S,14'S,17'R,18'S)-2',6',6',18'-tetramethylspiro[1,3-dioxolane-2,11'-5,7-dioxapentacyclo[11.7.0.02,10.04,8.014,18]icosane]-17'-yl]heptane-3,4-diol
• CAS: 91708-76-8
• 化学式: C₃₃H₅₆O₆
• 分子量: 548.804
• InChiKey: KOOFMZKIHYAQDO-YWTLOUHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol 在 三氟过氧乙酸 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以53%的产率得到芸苔素内酯
  参考文献：
  名称：

  Concise, Improved Procedure for the Synthesis of Brassinolide and Some Novel Side-Chain Analogues

  摘要：

  DOI：

  10.1021/jo961854y
• 作为产物：
  描述：

  2,2-二甲基-1,3-二氧环戊烷 在 对甲苯磺酸 sodium tetrahydroborate 、 disodium hydrogenphosphate 、 正丁基锂 、 氢气 、 nickel diacetate 、 碳酸氢钠 、 臭氧 、 乙二胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 37.0h， 生成 (2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol
  参考文献：
  名称：

  Aburatani, Masakazu; Takeuchi, Tadashi; Mori, Kenji, Agricultural and Biological Chemistry, 1985, vol. 49, # 12, p. 3557 - 3562

  摘要：

  DOI：

文献信息

• A new synthesis of castasterone and brassinolide from stigmasterol. A concise and stereoselective elaboration of the side chain from a C-22 aldehyde
  作者：Thomas G. Back、Peter G. Blazecka、M. Vijaya Krishna

  DOI：10.1139/v93-022

  日期：1993.2.1

  Brassinolide (1) and castasterone (2) were prepared from aldehyde 7, in turn available from stigmasterol (3). The addition of (E)-1-propenyllithium to 7, followed by diastereoselective Sharpless epoxidation of allylic alcohol 8 using (L)-(+)-diethyl tartrate, and regioselective epoxide-opening of (threo) epoxy alcohol 15 with isopropylmagnesium chloride in the presence of a catalytic amount of cuprous

  芸苔素内酯 (1) 和蓖麻酮 (2) 由醛 7 制备，而醛 7 又可从豆甾醇 (3) 获得。将 (E)-1-丙烯基锂添加到 7，然后使用 (L)-(+)-酒石酸二乙酯对烯丙醇 8 进行非对映选择性 Sharpless 环氧化，并使用异丙基氯化镁对 (threo) 环氧醇 15 进行区域选择性环氧化开环催化量的氰化亚铜的存在提供了二醇 17。使用更简单的模型醛 4 更详细地研究了环氧化和铜酸盐加成步骤。17 的水解提供了 2，它被 Baeyer 优先转化为 1 或其区域异构体 22-分别用三氟过氧乙酸或过氧硒酸进行 Villiger 氧化。
• Improved synthesis of brassinolide.
  作者：Masayuki SAKAKIBARA、Kenji MORI

  DOI：10.1271/bbb1961.47.663

  日期：——
• Synthesis of castasterone and formal synthesis of brassinolide from stigmasterol via a selenosulfonation approach
  作者：Thomas G. Back、M. Vijaya Krishna

  DOI：10.1021/jo00001a089

  日期：1991.1
• Bioactivity of brassinolide methyl ethers
  作者：Weide Luo、Loeke Janzen、Richard P. Pharis、Thomas G. Back

  DOI：10.1016/s0031-9422(97)00881-9

  日期：1998.10

  Four new derivatives of brassinolide (RR) were prepared by single or multiple methylation of the hydroxyl groups at C-2, C-3, C-22 and or C-23 to afford (22R,23R,24S)-2 alpha,3 alpha,23-trihydroxy-22-methoxy-7-oxa-7a-homo-5 alpha-ergostan-6-one (22-MeBR), (22R,23R,24S)-2 alpha,3 alpha,22-trihydroxy-23-methoxy-7-oxa-7a-homo-5 alpha-ergostan-6-one (23-MeBR),(22R,23R,24S)-2 alpha,3 alpha-dihydroxy-22,23-dimethoxy-7-oxa-7a-homo-5 alpha-ergostan-6-one (diMeBR), and (22R,23R,24S)-2 alpha,3 alpha,22,23-tetramethoxy-7-oxa-7a-homo-5 alpha-ergostan-6-one (tetraMeBR). The formation of methyl ethers is expected to block glycosylation of the free hydroxyl groups, which should prevent potential metabolic deactivation of these compounds by plants when. they are applied exogenously. The above BR derivatives were subjected to the rice leaf lamina inclination assay, in comparison with BR, to test for brassinosteroid activity. Whereas tetraMeBR and 23-MeBR showed negligible and very low activity, respectively, even at the high dosage of 1000 ng/plant, 22-MeBR showed weak activity relative to BR at low doses (1-10 ng/plant), and appreciable activity at high doses (1000 ng/plant). Of the four new compounds, diMeBR was the most active, comparable to 24-epibrassinolide (24-epiBR) at low to medium doses, and comparable to BR at doses of 1000 ng/plant. Thus, diMeBR is a good candidate for further investigation of persistence. As is the case for BR, a strong synergistic effect was observed when 22-MeBR or diMeBR were administered together with the auxin, indole-3-acetic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.