(3aR,6S,6aS)-4-hydroxy-6-tetradecyl-3a,4,6,6a-tetrahydro-3H-furo[3,4-d][1,3]oxazol-2-one | 1094615-99-2

• 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: (3aR,6S,6aS)-4-hydroxy-6-tetradecyl-3a,4,6,6a-tetrahydro-3H-furo[3,4-d][1,3]oxazol-2-one
• CAS: 1094615-99-2
• 化学式: C₁₉H₃₅NO₄
• 分子量: 341.491
• InChiKey: ROUQDCCNYXBLBG-LNAREIQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,6S,6aS)-4-hydroxy-6-tetradecyl-3a,4,6,6a-tetrahydro-3H-furo[3,4-d][1,3]oxazol-2-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 以32%的产率得到(3aS,6S,6aS)-6-tetradecyltetrahydrofuro[3,4-d]oxazol-2(3H)-one
  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 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 (3aR,6S,6aS)-4-hydroxy-6-tetradecyl-3a,4,6,6a-tetrahydro-3H-furo[3,4-d][1,3]oxazol-2-one
  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

• Stereocontrolled synthesis of cytotoxic anhydrosphingosine pachastrissamine by using [3.3] sigmatropic rearrangement of allyl cyanate
  作者：Yoshiyasu Ichikawa、Kenshi Matsunaga、Toshiya Masuda、Hiyoshizo Kotsuki、Keiji Nakano

  DOI：10.1016/j.tet.2008.09.036

  日期：2008.12

  A new route for the synthesis of the cytotoxic anhydrosphingosine pachastrissamine has been developed. [3.3] Sigmatropic rearrangement of an allyl cyanate was employed to construct the allyl amine moiety in 2 from the chiral C-4 unit 3. Oxidative cleavage of the double bond in 2, followed by THF ring formation furnished the target pachastrissamine.

  已经开发了合成细胞毒性脱水鞘氨醇pachastrissamine的新途径。[3.3]烯丙基氰酸酯的σ迁移重排用于构造烯丙基胺部分在2从手性C-4单元3。2中双键的氧化裂解，然后形成THF环，提供了目标pachastrissamine。