(3aR,6S,6aS)-6-tetradecyl-3,3a,6,6a-tetrahydrofuro[3,4-d][1,3]oxazole-2,4-dione | 1449490-42-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3aR,6S,6aS)-6-tetradecyl-3,3a,6,6a-tetrahydrofuro[3,4-d][1,3]oxazole-2,4-dione
• CAS: 1449490-42-9
• 化学式: C₁₉H₃₃NO₄
• 分子量: 339.475
• InChiKey: BEZRGOAMAHZPPS-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6S,6aS)-6-tetradecyl-3,3a,6,6a-tetrahydrofuro[3,4-d][1,3]oxazole-2,4-dione 在 三乙基硅烷 、 三氟化硼乙醚 、 二异丁基氢化铝 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 55.5h， 生成 jaspine B
  参考文献：
  名称：

  Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)

  摘要：

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.

  DOI：

  10.1021/jo4013223
• 作为产物：
  描述：

  1-十一烯 在 Hoveyda-Grubbs catalyst second generation 、 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (3aR,6S,6aS)-6-tetradecyl-3,3a,6,6a-tetrahydrofuro[3,4-d][1,3]oxazole-2,4-dione
  参考文献：
  名称：

  Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)

  摘要：

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.

  DOI：

  10.1021/jo4013223

文献信息

• Total Synthesis of the Cytotoxic Anhydrophytosphingosine Pachastrissamine (Jaspine B)
  作者：Vijay Dhand、Stanley Chang、Robert Britton

  DOI：10.1021/jo4013223

  日期：2013.8.16

  A short, 8-step synthesis of the marine natural product pachastrissamine has been developed that relies on a diastereoselective aldol reaction between a suitably protected hydantoin and an optically enriched alpha-chloroaldehyde. This synthetic route provides new opportunities for exploring structure activity relationships within this family of natural products.