(2S,4S)-3-Benzoyl-4-benzyl-2-isopropyl-6-methoxy-2,3,4,5-tetrahydro-pyrimidine-4-carboxylic acid methyl ester | 211686-58-7

• 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: (2S,4S)-3-Benzoyl-4-benzyl-2-isopropyl-6-methoxy-2,3,4,5-tetrahydro-pyrimidine-4-carboxylic acid methyl ester
• 英文别名: methyl (2S,4S)-3-benzoyl-4-benzyl-6-methoxy-2-propan-2-yl-2,5-dihydropyrimidine-4-carboxylate
• CAS: 211686-58-7
• 化学式: C₂₄H₂₈N₂O₄
• 分子量: 408.497
• InChiKey: ITNJUHDVLZFPDS-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-3-Benzoyl-4-benzyl-2-isopropyl-6-methoxy-2,3,4,5-tetrahydro-pyrimidine-4-carboxylic acid methyl ester 在 盐酸 、 Dowex 50W X 8 作用下， 生成 (S)-α-benzylaspartic acid
  参考文献：
  名称：

  α-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center:  Enantioselective Synthesis of α-Substituted Aspartic Acids^1,2

  摘要：

  A convenient method for the alpha-alkylation of (S)-asparagine with "self-regeneration of the stereogenic center" is described. The synthetic protocol involves stereoselective conversion of (S)-asparagine into enantiopure imino ether (2S,6S)-9, which is then alkylated with complete diastereoselectivity to give trans products 10-13 in good yields. Hydrolysis of these alkylated heterocycles is accomplished under mild acidic conditions to give the desired, enantiopure alpha-alkyl aspartic acids in excellent yields.

  DOI：

  10.1021/jo980367a
• 作为产物：
  描述：

  1-benzoyl-2(S)-isopropyl-6(S)-carboxy-perhydropyrimidin-4-one 在 silver(l) oxide 、 lithium diisopropyl amide 作用下， 反应 75.5h， 生成 (2S,4S)-3-Benzoyl-4-benzyl-2-isopropyl-6-methoxy-2,3,4,5-tetrahydro-pyrimidine-4-carboxylic acid methyl ester
  参考文献：
  名称：

  α-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center:  Enantioselective Synthesis of α-Substituted Aspartic Acids^1,2

  摘要：

  A convenient method for the alpha-alkylation of (S)-asparagine with "self-regeneration of the stereogenic center" is described. The synthetic protocol involves stereoselective conversion of (S)-asparagine into enantiopure imino ether (2S,6S)-9, which is then alkylated with complete diastereoselectivity to give trans products 10-13 in good yields. Hydrolysis of these alkylated heterocycles is accomplished under mild acidic conditions to give the desired, enantiopure alpha-alkyl aspartic acids in excellent yields.

  DOI：

  10.1021/jo980367a

文献信息

• α-Alkylation of (<i>S</i>)-Asparagine with Self-Regeneration of the Stereogenic Center:  Enantioselective Synthesis of α-Substituted Aspartic Acids¹^,²
  作者：Eusebio Juaristi、Heraclio López-Ruiz、Domingo Madrigal、Yara Ramírez-Quirós、Jaime Escalante

  DOI：10.1021/jo980367a

  日期：1998.7.1

  A convenient method for the alpha-alkylation of (S)-asparagine with "self-regeneration of the stereogenic center" is described. The synthetic protocol involves stereoselective conversion of (S)-asparagine into enantiopure imino ether (2S,6S)-9, which is then alkylated with complete diastereoselectivity to give trans products 10-13 in good yields. Hydrolysis of these alkylated heterocycles is accomplished under mild acidic conditions to give the desired, enantiopure alpha-alkyl aspartic acids in excellent yields.