[26,28-2H6]castasterone | 105075-67-0

• 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: [26,28-2H6]castasterone
• 英文别名: <26,28-2H6>castasterone；(2R,3S,5S,8S,9S,10R,13S,14S,17R)-2,3-dihydroxy-10,13-dimethyl-17-[(2S,3R,4R,5S)-7,7,7-trideuterio-3,4-dihydroxy-6-methyl-5-(trideuteriomethyl)heptan-2-yl]-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 105075-67-0
• 化学式: C₂₈H₄₈O₅
• 分子量: 470.638
• InChiKey: VYUIKSFYFRVQLF-ROXATJRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [26,28-2H6]castasterone 在 氨 、 lithium 作用下， 反应 1.0h， 以80.4%的产率得到[26,28-2H6]6α-hydroxycastasterone
  参考文献：
  名称：

  Biosynthesis of brassinosteroids in cultured cells of Catharanthus roseus

  摘要：

  Precursor administration experiments with H-2-labeled 6-oxocampestanol, 6-droxocastasterone and 6 alpha-hydroxycastasterone in cultured cells of Catharanthus roseus were performed and the metabolites were analyzed by GC-MS. [H-2(6)]Cathasterone was identified as a metabolite of [H-2(6)]6-oxocampestanol. whereas [H-2(6)]6 alpha-hydroxycastasterone and [H-2(6)]castasterone were identified as metabolites of [H-2(6)]6-deoxocastasterone, and [H-1(6)]castasterone was identified as a metabolite of [H-2(6)]6 alpha-hydroxycastasterone, indicating that 6-deoxocastasterone is converted to castasterone via 6 alpha-hydroxycastasterone. In addition, 6-deoxocathasterone, a putative biosynthetic intermediate in the late C6-oxidation pathway, was identified as an endogenous brassinosteroid. These studies provide further evidence supporting our proposed biosynthetic pathways for brassinolide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00582-8
• 作为产物：
  描述：

  (3S,5S,8S,9S,10R,13S,14S,17R)-17-((S)-1-((4R,5R)-2,2-dimethyl-5-((2S,3S)-3-methylbutan-2-yl-1,1,1,4,4,4-d6)-1,3-dioxolan-4-yl)ethyl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl methanesulfonate 在 四氧化锇 、 lithium carbonate 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 [26,28-2H6]castasterone
  参考文献：
  名称：

  Takatsuto, Suguru; Ikekawa, Nobuo, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 3, p. 1415 - 1418

  摘要：

  DOI：

文献信息

• A new synthesis of [26,28-2H6]brassinolide and [26,28-2H6]castasterone via an unusual methyl migration
  作者：A. Kolbe、A. Porzel、J. Schmidt、G. Adam

  DOI：10.1002/jlcr.662

  日期：2003.3.15

  Deuterium-labelled brassinosteroids, namely [26,28-2H6]castasterone, 8, and [26,28-2H6]brassinolide, 9, were synthesized starting from 6,6- ethylenedioxy-20-formyl-2α,3α-isopropylidenedioxy-5α-pregnane, 1, and 3-[2H3]methyl-but-1-yne-[4,4,4-2H3], 11. Upon alkylating cleavage of the epoxide 6 with trimethylaluminium-n-butyllithium an unusual migration of a neighbouring [2H3]methyl group takes place

  氘标记的油菜素类固醇，即 [26,28-2H6]castasterone, 8 和 [26,28-2H6] 油菜素内酯, 9，是从 6,6- ethylenedioxy-20-formyl-2α,3α-isopropylidenedioxy-5α 合成的-pregnane, 1, and 3-[2H3]methyl-but-1-yne-[4,4,4-2H3], 11. 用三甲基铝-正丁基锂对环氧化物 6 进行烷基化裂解后，相邻的不寻常迁移[2H3] 甲基在 26 和 28 位发生氘化。 版权所有 © 2002 John Wiley & Sons, Ltd。
• Takatsuto, Suguru; Ikekawa, Nobuo, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 10, p. 4045 - 4049
  作者：Takatsuto, Suguru、Ikekawa, Nobuo

  DOI：——

  日期：——