(2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone | 144413-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone
• 英文别名: [(1S)-3-methyl-1-[(2R,4S)-5-oxo-4-propan-2-yloxolan-2-yl]butyl] methanesulfonate
• CAS: 144413-08-1
• 化学式: C₁₃H₂₄O₅S
• 分子量: 292.397
• InChiKey: LPYBFBPGWCPWOX-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone 在 PEG 300 、 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 22.0h， 以83.5%的产率得到(2S,4R,5R)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone
  参考文献：
  名称：

  Synthesis of the hydroxyethylene isostere of Leu-Val

  摘要：

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.

  DOI：

  10.1021/jo00051a005
• 作为产物：
  描述：

  (S)-2-(3-Isobutyl-oxiranylmethyl)-3-methyl-N-((S)-1-phenyl-ethyl)-butyramide 在 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2S,4R,5S)-4-hydroxy-5-<(methanesulfonyl)oxy>-2-isopropyl-7-methyloctanoic acid, γ-lactone
  参考文献：
  名称：

  Synthesis of the hydroxyethylene isostere of Leu-Val

  摘要：

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.

  DOI：

  10.1021/jo00051a005

文献信息

• Synthesis of the hydroxyethylene isostere of Leu-Val
  作者：Peter G. M. Wuts、Allen R. Ritter、Lynn E. Pruitt

  DOI：10.1021/jo00051a005

  日期：1992.12

  The hydroxyethylene isostere of the dipeptide leu-val was synthesized from isovaleryl aldehyde in nine steps in 15% overall yield without the use of chromatographic separations. A key finding is the ability of an amide to selectively direct an epoxidation in an acyclic system and that the selectivity is a function of the amide's size.