(S)-5-hydroxy-5-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-3-methylenepentyl benzoate | 1236147-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-hydroxy-5-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-3-methylenepentyl benzoate
• 英文别名: [(5S)-5-hydroxy-5-[2-[(Z,3R)-3-methoxy-2-methylbut-1-enyl]-1,3-oxazol-4-yl]-3-methylidenepentyl] benzoate
• CAS: 1236147-00-4
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: YTKBVJQKLIWHIB-OFGXXTFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-5-hydroxy-5-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-3-methylenepentyl benzoate 在 三乙烯二胺 、 potassium hexacyanoferrate(III) 、 四氧化锇 、 碳酸氢钠 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Enigmazole A from Cinachyrella enigmatica. Bidirectional Bond Constructions with an Ambident 2,4-Disubstituted Oxazole Synthon

  摘要：

  The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.

  DOI：

  10.1021/ja1016975
• 作为产物：
  描述：

  (R,Z)-2-(3-methoxy-2-methylbut-1-enyl)oxazole-4-carbaldehyde 、 3-((tributylstannyl)methyl)but-3-enyl benzoate 在 三溴化硼 、 (1S,2S)-N,N-p-二甲苯磺酰基-1,2-二苯-1,2-乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到(S)-5-hydroxy-5-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-3-methylenepentyl benzoate
  参考文献：
  名称：

  Total Synthesis of Enigmazole A from Cinachyrella enigmatica. Bidirectional Bond Constructions with an Ambident 2,4-Disubstituted Oxazole Synthon

  摘要：

  The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.

  DOI：

  10.1021/ja1016975

文献信息

• Total Synthesis of Enigmazole A from <i>Cinachyrella enigmatica</i>. Bidirectional Bond Constructions with an Ambident 2,4-Disubstituted Oxazole Synthon
  作者：Colin K. Skepper、Tim Quach、Tadeusz F. Molinski

  DOI：10.1021/ja1016975

  日期：2010.8.4

  The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type coupling of an oxazol-2-ylzinc reagent formed directly from the parent ethyl 2-iodooxazole-4-carboxylate by zinc insertion. Other key steps include a hetero-Diels-Alder cycloaddition to form the central embedded pyran ring, a Wittig reaction to unite Eastern and Western hemispheres, and a ring size-selective Keck macrolactonization.