tert-butyl (3R)-5-hydroxy-3-(phenylmethoxycarbonylamino)pentanoate | 173675-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (3R)-5-hydroxy-3-(phenylmethoxycarbonylamino)pentanoate
• CAS: 173675-05-3
• 化学式: C₁₇H₂₅NO₅
• 分子量: 323.389
• InChiKey: XYNATOYOJFWPMT-CQSZACIVSA-N

物化性质

• 沸点：
  476.6±45.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-5-hydroxy-3-(phenylmethoxycarbonylamino)pentanoate 在 草酰氯 、 TEA 、 二甲基亚砜 作用下， 以93%的产率得到tert-butyl (3R)-5-oxo-3-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7
• 作为产物：
  描述：

  N-苄氧羰基-L-天门冬氨酸 4-叔丁酯 在 N-甲基吗啉 、 lithium hydroxide 、 sodium tetrahydroborate 、 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.0h， 生成 tert-butyl (3R)-5-hydroxy-3-(phenylmethoxycarbonylamino)pentanoate
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7