Botcinins D | 874911-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: Botcinins D
• 英文别名: [(4aR,6S,7R,8R,8aS)-3,4a,6,8-tetramethyl-2-oxo-6,7,8,8a-tetrahydropyrano[3,2-b]pyran-7-yl] (E,4S)-4-hydroxyoct-2-enoate
• CAS: 874911-31-6
• 化学式: C₂₀H₃₀O₆
• 分子量: 366.455
• InChiKey: QJUKURZOKSVYNB-QMYRPDPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3R,4R,4aS,8aR)-2,4,7,8a-tetramethyl-6-oxo-2,3,4,4a,6,8a-hexahydropyrano[3,2-b]pyran-3-yl (S,E)-4-((tert-butyldimethylsilyl)oxy)oct-2-enoate 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到Botcinins D
  参考文献：
  名称：

  Asymmetric Total Synthesis of Botcinins C, D, and F

  摘要：

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

  DOI：

  10.1021/ol801066y

文献信息

• Botcinins A, B, C, and D, Metabolites Produced by <i>Botrytis </i><i>c</i><i>inerea</i>, and Their Antifungal Activity against <i>Magnaporthe </i><i>g</i><i>risea</i>, a Pathogen of Rice Blast Disease
  作者：H. Tani、H. Koshino、E. Sakuno、H. Nakajima

  DOI：10.1021/np0503855

  日期：2005.12.1

  Four new metabolites, botcinins A-D (1-4), were isolated from the culture filtrate of a strain of Botrytis cinerea. Their structures were determined by spectroscopic methods, mainly NMR techniques, molecular modeling, and the modified Mosher's method. They exhibited antifungal activities against Magnaporthe grisea, a pathogen of rice blast disease. Botcinins B and C have a MIC of 12.5 mu M, and botcinins A and D are not active below 100 mu M.
• Asymmetric Total Synthesis of Botcinins C, D, and F
  作者：Hiroki Fukui、Isamu Shiina

  DOI：10.1021/ol801066y

  日期：2008.7.17

  Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and Sml(12)-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.

表征谱图