tert-butyl (3S)-2,2-dimethyl-4-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-carboxylate | 176217-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: tert-butyl (3S)-2,2-dimethyl-4-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-carboxylate
• CAS: 176217-49-5
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: UPWXMJPGTHLKIO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸甲酯 、 tert-butyl (3S)-2,2-dimethyl-4-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-carboxylate 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以89%的产率得到methyl (2S)-2-[[(2S)-3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)butanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  A new and versatile procedure for the incorporation of α,β-diamino acids into peptides

  摘要：

  A new route to peptide segments incorporating alpha,beta-diamino acids either at the alpha- or beta-positions is provided by enzymeimimetic ring opening of 3-amino beta-lactams with alpha-amino acid esters promoted by sodium azide or potassium cyanide.

  DOI：

  10.1039/cc9960000633
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (3S)-3-<(benzyloxycarbonyl)amino>-4,4-dimethylazetidin-2-one 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 tert-butyl (3S)-2,2-dimethyl-4-oxo-3-(phenylmethoxycarbonylamino)azetidine-1-carboxylate
  参考文献：
  名称：

  A new and versatile procedure for the incorporation of α,β-diamino acids into peptides

  摘要：

  A new route to peptide segments incorporating alpha,beta-diamino acids either at the alpha- or beta-positions is provided by enzymeimimetic ring opening of 3-amino beta-lactams with alpha-amino acid esters promoted by sodium azide or potassium cyanide.

  DOI：

  10.1039/cc9960000633

文献信息

• MONOBACTAMS AND METHODS OF THEIR SYNTHESIS AND USE
  申请人：PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：US20160326157A1

  公开（公告）日：2016-11-10

  Described herein are monobactam antibiotics of Formula (I), (I′), (II), and (II′), along with methods and intermediates for preparing these compounds. Pharmaceutical compositions and methods of treating infectious diseases using the monobactams are also provided.
• A new and versatile procedure for the incorporation of α,β-diamino acids into peptides
  作者：Claudio Palomo、Jesus M. Aizpurua、Regina Galarza、Antonia Mielgo

  DOI：10.1039/cc9960000633

  日期：——

  A new route to peptide segments incorporating alpha,beta-diamino acids either at the alpha- or beta-positions is provided by enzymeimimetic ring opening of 3-amino beta-lactams with alpha-amino acid esters promoted by sodium azide or potassium cyanide.