elansolid B1 | 1185198-94-0

• 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: elansolid B1
• 英文别名: (2E,4E,7R,8R,9R,10Z,12E,14Z)-15-[(1R,3aR,4R,5R,7aR)-1-hydroxy-4-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-1,3,3,6-tetramethyl-3a,4,5,7a-tetrahydro-2H-inden-5-yl]-7,9-dihydroxy-4,8-dimethylpentadeca-2,4,10,12,14-pentaenoic acid
• CAS: 1185198-94-0
• 化学式: C₃₇H₅₀O₇
• 分子量: 606.8
• InChiKey: FSKQADSFEYMILN-ROZCPUIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  138
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  elansolid B1 、 三甲基硅烷化重氮甲烷 以 甲醇 、 甲苯 为溶剂， 以31%的产率得到elansolid B1 methyl ester
  参考文献：
  名称：

  Total Synthesis of the Antibiotic Elansolid B1

  摘要：

  The antibiotic elansolid B1 was prepared by a convergent strategy that relied on a highly diastereoselective, biomimetic intramolecular Diels-Alder cycloaddition (IMDA) that furnished the tetrahydroindane unit. Other key features are a double Sonogashira cross-coupling and a substrate-controlled Yamamoto aldol reaction.

  DOI：

  10.1021/ol403441c
• 作为产物：
  描述：

  (1R,3aR,4R,5S,7aR)-5-ethynyl-4-[(R)-hydroxy(4-hydroxyphenyl)methyl]-1,3,3,6-tetramethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-1-ol 在 copper(l) iodide 、 四(三苯基膦)钯 、 camphor-10-sulfonic acid 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氘代甲醇-d 、 丙酮 为溶剂， 反应 231.0h， 生成 elansolid B1
  参考文献：
  名称：

  Total Synthesis of the Antibiotic Elansolid B1

  摘要：

  The antibiotic elansolid B1 was prepared by a convergent strategy that relied on a highly diastereoselective, biomimetic intramolecular Diels-Alder cycloaddition (IMDA) that furnished the tetrahydroindane unit. Other key features are a double Sonogashira cross-coupling and a substrate-controlled Yamamoto aldol reaction.

  DOI：

  10.1021/ol403441c

文献信息

• Elansolid A, a Unique Macrolide Antibiotic from Chitinophaga sancti Isolated as Two Stable Atropisomers
  作者：Heinrich Steinmetz、Klaus Gerth、Rolf Jansen、Nadin Schläger、Richard Dehn、Silke Reinecke、Andreas Kirschning、Rolf Müller

  DOI：10.1002/anie.201005226

  日期：2011.1.10

  Elansolid A was isolated from Chitinophaga sancti (Flexibacter sancti ) as the two separable isomers A1 and A2 (1 and 1*, respectively). Molecular modeling revealed that they are stable atropisomers which are “frozen” by 14 inflexible bonds within the 19‐membered macrolide ring. The absolute configuration was established by synthesis of the C1–C11 fragment. Elansolid A2 shows activity against Gram‐positive

  僵化性：从两个壳多糖（San Chitiophaga sancti（Flexibacter sancti  ））中分离得到了Elansolid A，它是两个可分离的异构体A1和A2（分别为1和1 *）。分子模型显示它们是稳定的阻转异构体，被19元大环内酯环内的14个刚性键“冻结”。绝对构型是通过合成C1-C11片段而建立的。Elansolid A2对革兰氏阳性细菌具有活性。
• Total Synthesis of the Antibiotic Elansolid B1
  作者：Arne Weber、Richard Dehn、Nadin Schläger、Bastian Dieter、Andreas Kirschning

  DOI：10.1021/ol403441c

  日期：2014.1.17

  The antibiotic elansolid B1 was prepared by a convergent strategy that relied on a highly diastereoselective, biomimetic intramolecular Diels-Alder cycloaddition (IMDA) that furnished the tetrahydroindane unit. Other key features are a double Sonogashira cross-coupling and a substrate-controlled Yamamoto aldol reaction.