methyl 7-ketomonate A 13-tert-butyldimethylsilyl ether | 1314406-70-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 7-ketomonate A 13-tert-butyldimethylsilyl ether
• 英文别名: methyl (E)-4-[(2S,3S,5S)-5-[[(2S,3S)-3-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxybutan-2-yl]oxiran-2-yl]methyl]-3-hydroxy-4-oxooxan-2-yl]-3-methylbut-2-enoate
• CAS: 1314406-70-6
• 化学式: C₂₄H₄₂O₇Si
• 分子量: 470.679
• InChiKey: PTYFTMFDDOARKD-ZPVMKOLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 7-ketomonate A 13-tert-butyldimethylsilyl ether 在 potassium hydrogensulfate 、 水 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以21%的产率得到methyl (E)-4-[(1R,2S,3S,6R,8R,9S,10S,11S)-2,8-dihydroxy-10,11-dimethyl-4,12,13-trioxatricyclo[7.3.1.01,6]tridecan-3-yl]-3-methylbut-2-enoate
  参考文献：
  名称：

  Mupirocin F: structure elucidation, synthesis and rearrangements

  摘要：

  The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.021
• 作为产物：
  描述：

  methyl monate A 在 吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 methyl 7-ketomonate A 13-tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Mupirocin F: structure elucidation, synthesis and rearrangements

  摘要：

  The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.021

文献信息

• Mupirocin F: structure elucidation, synthesis and rearrangements
  作者：Robert W. Scott、Annabel C. Murphy、Ji’en Wu、Joanne Hothersall、Russell J. Cox、Thomas J. Simpson、Christopher M. Thomas、Christine L. Willis

  DOI：10.1016/j.tet.2011.05.021

  日期：2011.7

  The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.