(2S,3S)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate

• 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,3S)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate
• 英文别名: 4-O-tert-butyl 1-O-ethyl (2S,3S)-3-amino-2-(4-methoxyanilino)butanedioate
• 化学式: C₁₇H₂₆N₂O₅
• 分子量: 338.404
• InChiKey: FCLSMRRBLDXIHM-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 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：
  99.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-二苯亚甲基-甘氨酸叔丁酯 、 Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 在 sodium hydroxide 、 (R,R)-3,4,5-F₃-C₆H₂-NAS-Br 作用下， 以 均三甲苯 为溶剂， 反应 6.0h， 生成 (2S,3S)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate 、 (2R,3S)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate 、 (2S,3R)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate 、 (2R,3R)-1-tert-butyl 4-ethyl 3-[N-(4-methoxyphenyl)amino]aspartate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions

  摘要：

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

  DOI：

  10.1021/ol049215u

文献信息

• Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions
  作者：Takashi Ooi、Minoru Kameda、Jun-ichi Fujii、Keiji Maruoka

  DOI：10.1021/ol049215u

  日期：2004.7.1

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.