methyl 7-keto-3β-acetoxy-25(S)-methyl-24-bishomo-5α-cholan-26-oate | 950602-07-0

• 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: methyl 7-keto-3β-acetoxy-25(S)-methyl-24-bishomo-5α-cholan-26-oate
• 英文别名: methyl (2S,6R)-6-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-7-oxo-1,2,3,4,5,6,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-methylheptanoate
• CAS: 950602-07-0
• 化学式: C₃₀H₄₈O₅
• 分子量: 488.708
• InChiKey: ZONMAUNCCRRJPB-XCLZZNMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 7-keto-3β-acetoxy-25(S)-methyl-24-bishomo-5α-cholan-26-oate 在 伯吉斯试剂 、 L-Selectride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 5.0h， 生成 methyl (2S,6R)-6-((3S,5S,9R,10S,13R,14R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methylheptanoate
  参考文献：
  名称：

  Stereocontrolled Synthesis of Dafachronic Acid A, the Ligand for the DAF-12 Nuclear Receptor of Caenorhabditis elegans

  摘要：

  An efficient synthetic route to the DAF-12 nuclear receptor ligand of C. elegans, dafachronic acid, is described that starts with the abundant plant sterol beta-stigmasterol and proceeds in 37% overall yield. The synthesis establishes the structure of this rare nematode hormone.

  DOI：

  10.1021/ja074306i
• 作为产物：
  描述：

  (22S)-6β-methoxy-3α,5-cyclo-5α-chol-23-en-22-ol 在 palladium on activated charcoal 3,5-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， -78.0~90.0 ℃ 、101.33 kPa 条件下， 反应 8.33h， 生成 methyl 7-keto-3β-acetoxy-25(S)-methyl-24-bishomo-5α-cholan-26-oate
  参考文献：
  名称：

  Stereocontrolled Synthesis of Dafachronic Acid A, the Ligand for the DAF-12 Nuclear Receptor of Caenorhabditis elegans

  摘要：

  An efficient synthetic route to the DAF-12 nuclear receptor ligand of C. elegans, dafachronic acid, is described that starts with the abundant plant sterol beta-stigmasterol and proceeds in 37% overall yield. The synthesis establishes the structure of this rare nematode hormone.

  DOI：

  10.1021/ja074306i

文献信息

• Divergent and stereoselective synthesis of dafachronic acids
  作者：Antimo Gioiello、Paola Sabbatini、Emiliano Rosatelli、Antonio Macchiarulo、Roberto Pellicciari

  DOI：10.1016/j.tet.2011.01.022

  日期：2011.3

  A new divergent synthesis of DAF-12 ligands, namely Delta(4)- and Delta(7)-dafachronic acid, is described starting from the natural bile acid hyodeoxycholic acid. Homologation of the side chain followed by stereoselective reduction of the Delta(24) olefinic linkage, 6 alpha-dehydroxylation and C-3-oxidation affords dafachronic acids in good yields and high diastereoselectivity making this approach easily accessible and scalable. (C) 2011 Elsevier Ltd. All rights reserved.
• Syntheses and Biological Evaluation of B-Ring-Modified Analogues of Dafachronic Acid A
  作者：Simon Giroux、Axel Bethke、Nicole Fielenbach、Adam Antebi、E. J. Corey

  DOI：10.1021/ol801425v

  日期：2008.8.21

  Synthesis and testing of dafachronic acid A (1) and its derivatives 2 and 3 have revealed that 1, and not a further oxidation product, is the natural ligand for the DAF-12 receptor of Caenorhabditis elegans.