tert-butyl (4S,5S,1'R)-5-(2'-N-(4-methoxybenzyl)amino-1'-hydroxyethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate | 736152-00-4

• 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: tert-butyl (4S,5S,1'R)-5-(2'-N-(4-methoxybenzyl)amino-1'-hydroxyethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
• 英文别名: tert-butyl (4S,5S)-5-[(1R)-1-hydroxy-2-[(4-methoxyphenyl)methylamino]ethyl]-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
• CAS: 736152-00-4
• 化学式: C₂₅H₃₃N₃O₆
• 分子量: 471.554
• InChiKey: QQYOFOHPKLQQKE-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5S,1'R)-5-(2'-N-(4-methoxybenzyl)amino-1'-hydroxyethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate 在 甲酸 、 二苯基磷酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 以65%的产率得到(3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione
  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
• 作为产物：
  描述：

  N-二苯亚甲基-甘氨酸叔丁酯 在 platinum(IV) oxide sodium hydroxide 、 (R,R)-3,4,5-F₃-C₆H₂-NAS-Br 、 氢气 、 二异丁基氢化铝 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 均三甲苯 为溶剂， 反应 26.0h， 生成 tert-butyl (4S,5S,1'R)-5-(2'-N-(4-methoxybenzyl)amino-1'-hydroxyethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
  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.