5-[(Tert-butyldimethylsilyl)oxy]hexanoic acid | 1649449-76-2

• 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: 5-[(Tert-butyldimethylsilyl)oxy]hexanoic acid
• 英文别名: 5-[tert-butyl(dimethyl)silyl]oxyhexanoic acid
• CAS: 1649449-76-2
• 化学式: C₁₂H₂₆O₃Si
• 分子量: 246.422
• InChiKey: PANDHPGJJCZSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(Tert-butyldimethylsilyl)oxy]hexanoic acid 在 4-二甲氨基吡啶 、 三(二甲氨基)锍二氟三甲基硅酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.33h， 生成 (R)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 5-hydroxy-2-((4R,5R,6R)-6-((E)-2-iodovinyl)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl)hexanoate
  参考文献：
  名称：

  Synthesis of Two Subunits of the Macrolide Domain of the Immunosuppressive Agent Sanglifehrin A and Assembly of a Macrolactone Precursor. Application of Masamune anti-Aldol Condensation

  摘要：

  Asymmetric anti-aldol coupling of a norephedrine-derived ester with an a-chiral aldehyde was used to synthesize a carboxylic acid representing the C13-C19 segment of the macrocyclic domain present in the immunosuppressive agent sanglifehrin A. Felkin addition set configuration at the C14-C17 stereotetrad in this unit in which hydroxyl functions at C15 and C17 were masked as an internal ketal. The carboxyl group of this segment was coupled to the N-terminus of the tripeptide portion (C1-N12) of sanglifehrin A macrolactone to assemble the C1-C19 domain. Synthesis of the C20-C25 subunit of sanglifehrin A containing a (23S) alcohol was completed via asymmetric allylation of (E)-3-iodo-2-methylprop-2-enal followed by oxidative cleavage of the terminal vinyl appendage and a Takai olefination with pinacol dichloromethylboronate. Esterification of this alcohol with a C1-C19 carboxylic acid furnished an open C1-C25 macrolactone precursor, but this substance failed to undergo macrocyclization via intramolecular SuzukiMiyaura coupling.

  DOI：

  10.1021/jo5027595
• 作为产物：
  描述：

  5-羟基己酸甲酯 在 咪唑 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 5-[(Tert-butyldimethylsilyl)oxy]hexanoic acid
  参考文献：
  名称：

  Synthesis of Two Subunits of the Macrolide Domain of the Immunosuppressive Agent Sanglifehrin A and Assembly of a Macrolactone Precursor. Application of Masamune anti-Aldol Condensation

  摘要：

  Asymmetric anti-aldol coupling of a norephedrine-derived ester with an a-chiral aldehyde was used to synthesize a carboxylic acid representing the C13-C19 segment of the macrocyclic domain present in the immunosuppressive agent sanglifehrin A. Felkin addition set configuration at the C14-C17 stereotetrad in this unit in which hydroxyl functions at C15 and C17 were masked as an internal ketal. The carboxyl group of this segment was coupled to the N-terminus of the tripeptide portion (C1-N12) of sanglifehrin A macrolactone to assemble the C1-C19 domain. Synthesis of the C20-C25 subunit of sanglifehrin A containing a (23S) alcohol was completed via asymmetric allylation of (E)-3-iodo-2-methylprop-2-enal followed by oxidative cleavage of the terminal vinyl appendage and a Takai olefination with pinacol dichloromethylboronate. Esterification of this alcohol with a C1-C19 carboxylic acid furnished an open C1-C25 macrolactone precursor, but this substance failed to undergo macrocyclization via intramolecular SuzukiMiyaura coupling.

  DOI：

  10.1021/jo5027595