(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 439589-14-7

• 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: (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1R,2S,4S)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 439589-14-7
• 化学式: C₃₉H₅₄N₂O₆S
• 分子量: 678.934
• InChiKey: PWSZRVJUOWCEHJ-YKIHUXOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氢气 、 (叔丁基亚氨基)三(吡咯烷)膦 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0~85.0 ℃ 、206.85 kPa 条件下， 反应 29.0h， 生成 (S)-α-benzylaspartic 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
• 作为产物：
  描述：

  (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  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

• 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%).