benzyl 4-<(benzyloxycarbonyl)amino>-5-hydroxypentanoate | 110559-89-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 4-<(benzyloxycarbonyl)amino>-5-hydroxypentanoate
• CAS: 110559-89-2
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: KMGYEILHZYWJDW-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 4-<(benzyloxycarbonyl)amino>-5-hydroxypentanoate 在 palladium on activated charcoal 四氮唑 、 1,4-环己二烯 、 氢气 、 碘 、 三氟乙酸 、 sodium iodide 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 水 、 乙腈 、 丁酮 为溶剂， 反应 57.17h， 生成
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082
• 作为产物：
  描述：

  (S)-4-Benzyloxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 benzyl 4-<(benzyloxycarbonyl)amino>-5-hydroxypentanoate
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082

文献信息

• Asymmetric Michael Addition of Malonates to Enones Catalyzed by a Primary β-Amino Acid and Its Lithium Salt
  作者：Masanori Yoshida、Mao Narita、Shoji Hara

  DOI：10.1021/jo201429w

  日期：2011.10.21

  Highly enantioselective Michael addition of malonates to enones was achieved using a mixed catalyst consisting of a primary β-amino acid, O-TBDPS (S)-β-homoserine, and its lithium salt. Various cyclic and acyclic enones were converted into 1,5-ketoesters in high yields (up to 92%) with high enantioselectivity (up to 97% ee) under mild reaction conditions. Details of synthesis of the catalyst, optimization

  使用由伯β-氨基酸，O - TBDPS（S）-β-高丝氨酸及其锂盐组成的混合催化剂，实现了丙二酸酯向烯酮的高度对映选择性迈克尔加成。在温和的反应条件下，各种环状和无环烯酮以高对映选择性（高达97％ee）高收率（高达92％）转化为1,5-酮酸酯。描述了催化剂的合成，迈克尔加成反应的反应条件的优化以及合理的反应机理的细节。