methyl (R)-5-formyl-5-hydroxyhexadecanoate | 959781-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (R)-5-formyl-5-hydroxyhexadecanoate
• 英文别名: methyl (5R)-5-formyl-5-hydroxyhexadecanoate
• CAS: 959781-10-3
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: MDQGCIQMZCRHMU-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-5-formyl-5-hydroxyhexadecanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以97%的产率得到(R)-5-hydroxy-5-(hydroxymethyl)hexadecanoic acid methyl ester
  参考文献：
  名称：

  Concise asymmetric synthesis of (R)-(+)-tanikolide

  摘要：

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.012
• 作为产物：
  描述：

  4-溴原丁酸三甲酯 在 盐酸 、 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 methyl (R)-5-formyl-5-hydroxyhexadecanoate
  参考文献：
  名称：

  Concise asymmetric synthesis of (R)-(+)-tanikolide

  摘要：

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.09.012

文献信息

• Concise asymmetric synthesis of (R)-(+)-tanikolide
  作者：Chenxia Zhang、Naoya Hosoda、Masatoshi Asami

  DOI：10.1016/j.tetasy.2007.09.012

  日期：2007.9

  A highly stereoselective total synthesis of (R)-(+)-tanikolide, a delta-lactonic marine natural product, was accomplished in seven steps from easily available starting materials with a 51% overall yield. An asymmetric synthesis of an alpha-hydroxy aldehyde having a stereogenic quaternary center, by the use of (S)-2-(anilinomethyl) pyrrolidine as a chiral auxiliary, was employed in a key step. (c) 2007 Elsevier Ltd. All rights reserved.