(2R,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid δ-lactone | 103335-79-1

• 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: (2R,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid δ-lactone
• 英文别名: (2S,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid, γ-lactone；tert-butyl (S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-methylbutylcarbamate；tert-butyl N-[(1S)-3-methyl-1-[(2S,4S)-5-oxo-4-propan-2-yloxolan-2-yl]butyl]carbamate
• CAS: 103335-79-1
• 化学式: C₁₇H₃₁NO₄
• 分子量: 313.437
• InChiKey: OFRBOUZDDODHBW-IHRRRGAJSA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  438.2±18.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid δ-lactone 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2S,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-isopropyl-7-methyl-octanoic acid
  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：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 Rh on carbon 盐酸 、 potassium tert-butylate 、 氢气 、 lithium perchlorate 、 对甲苯磺酸 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~25.0 ℃ 、344.73 kPa 条件下， 反应 81.02h， 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：

  Synthesis of the dipeptide hydroxyethylene isostere of Leu-Val, a transition state mimic for the control of enzyme function

  摘要：

  DOI：

  10.1021/jo00254a016

文献信息

• Nishi, Takahide; Kataoka, Mitsuru; Morisawa, Yasuhiro, Chemistry Letters, 1989, p. 1993 - 1996
  作者：Nishi, Takahide、Kataoka, Mitsuru、Morisawa, Yasuhiro

  DOI：——

  日期：——
• On a Possible Neutral Charge State for the Catalytic Dyad in β-Secretase When Bound to Hydroxyethylene Transition State Analogue Inhibitors
  作者：Fredy Sussman、José M. Otero、M. Carmen Villaverde、Marian Castro、José L. Domínguez、Lucía González-Louro、Ramón J. Estévez、J. Carlos Estévez

  DOI：10.1021/jm101568y

  日期：2011.4.28

  beta-Secretase is one of the aspartic proteases involved in the formation of amyloid plaques in Alzheimer's disease patients Our previous results using a combination of surface plasmon resonance experiments with molecular Modeling calculations: suggested that the Asp dyad in beta-secretase bound to hydroxylethylene containing inhibitors adopts a neutral charged state. In this work, we show that the Asp dyad diprotonated state reproduced the binding ranking of a set of these inhibitors better than alternative protonation states.
• 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.
• NISHI, TAKAHIDE;KATAOKA, MITSURU;MORISAWA, YASUHIRO, CHEM. LETT.,(1989) N1, C. 1993-1996
  作者：NISHI, TAKAHIDE、KATAOKA, MITSURU、MORISAWA, YASUHIRO

  DOI：——

  日期：——
• WUTS, PETER G. M.;PUTT, STERLING R.;RITTER, ALLEN R., J. ORG. CHEM., 53,(1988) N 19, C. 4503-4508
  作者：WUTS, PETER G. M.、PUTT, STERLING R.、RITTER, ALLEN R.

  DOI：——

  日期：——