| 1236147-23-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 1236147-23-1
• 化学式: C₃₁H₆₀O₅Si₂
• 分子量: 568.985
• InChiKey: GOKWIRVADCCLNW-MJNQHXDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.02
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 原甲酸三甲酯 在 camphorsulfonic acid 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2S,4S,5S)-methyl 5-(tert-butyldimethylsilyloxy)-6-(4,4-dimethoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-2,4-dimethylhexanoate 、 (2S,4S,5S)-methyl 5-(tert-butyldimethylsilyloxy)-6-(4,4-dimethoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-2,4-dimethylhexanoate 、 (2S,4S,5S)-methyl 5-(tert-butyldimethylsilyloxy)-6-(4,4-dimethoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-2,4-dimethylhexanoate
  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：

  、 (2S,4S,5S)-methyl 5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-7-oxoheptanoate 在 三氟化硼乙醚 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 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