(2S,4S,5S)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone | 103335-76-8

• 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,4S,5S)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone
• 英文别名: (3S,5S)-5-[(1S)-1-azido-3-methylbutyl]-3-propan-2-yloxolan-2-one
• CAS: 103335-76-8
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: JJLMCSJFMPSXRN-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S,5S)-2-(2-propyl)-4-hydroxy-5-azido-7-methyloctanoic acid, γ-lactone 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 (2R,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid δ-lactone
  参考文献：
  名称：

  Design of Substrate-Based Inhibitors of Human β-Secretase

  摘要：

  By use of the effectively cleaved beta-secretase (BACE) substrate (1), incorporation of a statine in P-l resulted in a weak inhibitor 13 of the enzyme. Further substitution of P-1'-Asp by P-1'-Val in 13 results in a potent inhibitor 22 of BACE. Removal of the P-10-P-5 residues on the N-terminal part of inhibitor 22 resulted in no loss of potency (23). C-terminal truncations of inhibitor 22 generally led to significant loss of potency.

  DOI：

  10.1021/jm0155695
• 作为产物：
  描述：

  (E)-(S)-2-Isopropyl-7-methyl-oct-4-enoic acid ((S)-1-phenyl-ethyl)-amide 在 PEG 300 、 sodium azide 、 硫酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 29.67h， 生成 (2S,4S,5S)-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

文献信息

• Design of Substrate-Based Inhibitors of Human β-Secretase
  作者：Jay S. Tung、David L. Davis、John P. Anderson、Don E. Walker、Shumeye Mamo、Nancy Jewett、Roy K. Hom、Sukanto Sinha、Eugene D. Thorsett、Varghese John

  DOI：10.1021/jm0155695

  日期：2002.1.1

  By use of the effectively cleaved beta-secretase (BACE) substrate (1), incorporation of a statine in P-l resulted in a weak inhibitor 13 of the enzyme. Further substitution of P-1'-Asp by P-1'-Val in 13 results in a potent inhibitor 22 of BACE. Removal of the P-10-P-5 residues on the N-terminal part of inhibitor 22 resulted in no loss of potency (23). C-terminal truncations of inhibitor 22 generally led to significant loss of potency.
• 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.