(2S,3S)-Dimethyl N,N'-bis(benzyloxycarbonyl)-3-aminoaspartate

• 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)-Dimethyl N,N'-bis(benzyloxycarbonyl)-3-aminoaspartate
• 英文别名: N,N'-Bisbenzyloxycarbonyl-S,S-diaminobernsteinsaeure-dimethylester；dimethyl (2S,3S)-2,3-bis(phenylmethoxycarbonylamino)butanedioate
• 化学式: C₂₂H₂₄N₂O₈
• 分子量: 444.441
• InChiKey: NPPZVPFUKDPXJI-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate 在 palladium on activated charcoal 、 W-2 Raney Ni 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、358.53 kPa 条件下， 反应 7.83h， 生成 (2S,3S)-Dimethyl N,N'-bis(benzyloxycarbonyl)-3-aminoaspartate
  参考文献：
  名称：

  On the Stereoselectivity of the Reaction of N-(9-Phenylfluoren-9-yl)aspartate Enolates with Electrophiles. Synthesis of Enantiomerically Pure 3-Hydroxy-, 3-Amino-, and 3-Hydroxy-3-methylaspartates

  摘要：

  We have developed efficient and stereoselective preparations of enantiomerically pure (3R)- and (3S)-N-Pf-3-hydroxy- and N-Pf-3-aminoaspartates by reaction of N-Pf-aspartate enolates with electrophilic hydroxylating or aminating reagents. The stereoselectivity of the hydroxylation and amination reactions was shown to be dependent on the structure of the enolate (which is strongly affected by the presence of strong metal complexing agents) and whether the electrophile is able to complex the enolate counterion in the transition state of the reaction. We have also developed a regioselective preparation of enantiomerically pure N-Pf-3-hydroxy-3-methylaspartates, albeit with only modest stereoselectivity.

  DOI：

  10.1021/jo00104a019

文献信息

• Biernat,J.F.; Ludwicka,S., Roczniki Chemii, 1972, vol. 46, p. 1151 - 1156
  作者：Biernat,J.F.、Ludwicka,S.

  DOI：——

  日期：——
• On the Stereoselectivity of the Reaction of N-(9-Phenylfluoren-9-yl)aspartate Enolates with Electrophiles. Synthesis of Enantiomerically Pure 3-Hydroxy-, 3-Amino-, and 3-Hydroxy-3-methylaspartates
  作者：Eduardo Fernandez-Megia、Manuel M. Paz、F. Javier Sardina

  DOI：10.1021/jo00104a019

  日期：1994.12

  We have developed efficient and stereoselective preparations of enantiomerically pure (3R)- and (3S)-N-Pf-3-hydroxy- and N-Pf-3-aminoaspartates by reaction of N-Pf-aspartate enolates with electrophilic hydroxylating or aminating reagents. The stereoselectivity of the hydroxylation and amination reactions was shown to be dependent on the structure of the enolate (which is strongly affected by the presence of strong metal complexing agents) and whether the electrophile is able to complex the enolate counterion in the transition state of the reaction. We have also developed a regioselective preparation of enantiomerically pure N-Pf-3-hydroxy-3-methylaspartates, albeit with only modest stereoselectivity.