2-((4S,6S)-6-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanol | 1236147-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((4S,6S)-6-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanol
• CAS: 1236147-21-9
• 化学式: C₁₇H₂₇NO₅
• 分子量: 325.405
• InChiKey: UBEFCEBMHGSHDA-VFSDSTMQSA-N

物化性质

• 沸点：
  462.7±55.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.95
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-((4S,6S)-6-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到4-((4S,6R)-6-(2-iodoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazole
  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：

  2-((4S,6S)-6-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethyl benzoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以80%的产率得到2-((4S,6S)-6-(2-((R,Z)-3-methoxy-2-methylbut-1-enyl)oxazol-4-yl)-2,2-dimethyl-1,3-dioxan-4-yl)ethanol
  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