(S)-3-((E,4S,5R,6R)-5-(methoxymethoxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one | 1442693-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-3-((E,4S,5R,6R)-5-(methoxymethoxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one
• CAS: 1442693-39-1
• 化学式: C₁₉H₃₃NO₅
• 分子量: 355.475
• InChiKey: XYERBTJAHCEFMY-COYXHAGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((E,4S,5R,6R)-5-(methoxymethoxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.05h， 以90%的产率得到(S)-3-((2R,4S,5R,6R)-5-(methoxymethoxy)-2,4,6-trimethyloctanoyl)-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction

  摘要：

  A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukalyama aldol reaction and regio- and stereoselective reduction reactions. All Isomers were obtained selectively in a few steps. The short step synthesis of septoriamycin A, an antimalarial and antileishmanial agent, has been achieved by this methodology.

  DOI：

  10.1021/ol401406m
• 作为产物：
  描述：

  (4S)-3-[(2E,4S,5S,6E)-5-hydroxy-2,4,6-trimethylocta-2,6-dienoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 (1,5-环辛二烯)二(三苯基膦)六氟磷酸铑二氯甲烷络合物(1:1) 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 (S)-3-((E,4S,5R,6R)-5-(methoxymethoxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction

  摘要：

  A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukalyama aldol reaction and regio- and stereoselective reduction reactions. All Isomers were obtained selectively in a few steps. The short step synthesis of septoriamycin A, an antimalarial and antileishmanial agent, has been achieved by this methodology.

  DOI：

  10.1021/ol401406m