(R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid | 439589-35-2

• 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: (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid
• 英文别名: (2R)-2-benzyl-1-[(4-methoxyphenyl)methyl]-4-oxoazetidine-2-carboxylic acid
• CAS: 439589-35-2
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: UALMLQNOPCQTSB-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-酞酰亚胺基丙酸甲酯 、 (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 生成 Pmb-α-Bzl-Azn-L-Ala-OMe
  参考文献：
  名称：

  General Approach for the Stereocontrolled Construction of the β-Lactam Ring in Amino Acid-Derived 4-Alkyl-4-carboxy-2-azetidinones

  摘要：

  The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N-alpha-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).

  DOI：

  10.1021/jo025571j
• 作为产物：
  描述：

  Cbz,PMB-Phe-OH 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0 ℃ 、103.42 kPa 条件下， 反应 265.0h， 生成 (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid
  参考文献：
  名称：

  General Approach for the Stereocontrolled Construction of the β-Lactam Ring in Amino Acid-Derived 4-Alkyl-4-carboxy-2-azetidinones

  摘要：

  The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N-alpha-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).

  DOI：

  10.1021/jo025571j

文献信息

• Simple access to novel azetidine-containing conformationally restricted amino acids by chemoselective reduction of β-lactams
  作者：Guillermo Gerona-Navarro、Ma Angeles Bonache、Miriam Alı́as、Ma Jesús Pérez de Vega、Ma Teresa Garcı́a-López、Pilar López、Carlos Cativiela、Rosario González-Muñiz

  DOI：10.1016/j.tetlet.2004.01.023

  日期：2004.3

  Reduction with diphenylsilane and catalytic amounts of tris(triphenylphosphine)rhodium(I) carbonyl hydride resulted in an efficient, chemoselective method for the transformation of amino-acid-derived beta-lactams into the corresponding azetidines, which after removal of the p-methoxybenzyl group, afforded a new family of conformationally restricted amino acids. Phe-derived compounds were obtained in enantiopure form by combining HPLC resolution of the beta-lactam precursor and the above-mentioned procedure. (C) 2004 Elsevier Ltd. All rights reserved.
• General Approach for the Stereocontrolled Construction of the β-Lactam Ring in Amino Acid-Derived 4-Alkyl-4-carboxy-2-azetidinones
  作者：Guillermo Gerona-Navarro、M. Teresa García-López、Rosario González-Muñiz

  DOI：10.1021/jo025571j

  日期：2002.5.1

  The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the beta-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding N-alpha-chloroacetyl derivatives bearing (+)- or (-)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).