(2S,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate | 749253-92-7

• 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,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate
• 英文别名: ethyl (2S,3S)-2,3-diamino-3-phenylpropanoate
• CAS: 749253-92-7
• 化学式: C₁₁H₁₆N₂O₂
• 分子量: 208.26
• InChiKey: AQOCNRRHMCCNDH-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate 在 N,N'-羰基二咪唑 作用下， 生成 (4S,5S)-(+)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate
  参考文献：
  名称：

  Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates

  摘要：

  Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.03.001
• 作为产物：
  描述：

  (S,E)-N-benzylidene-4-methylbenzenesulfinamide 在 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 环己烷 为溶剂， 反应 14.33h， 生成 (2S,3S)-(+)-ethyl 2,3-diamino-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric Synthesis of syn-(2R,3S)- and anti-(2S,3S)-Ethyl Diamino-3-phenylpropanoates from N-(Benzylidene)-p-toluenesulfinamide and Glycine Enolates

  摘要：

  Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.

  DOI：

  10.1021/ol048981y

文献信息

• Asymmetric Synthesis of <i>s</i><i>yn</i>-(2<i>R</i>,3<i>S</i>)<i>- </i>and <i>a</i><i>nti</i>-(<i>2S</i>,3<i>S</i>)-Ethyl Diamino-3-phenylpropanoates from <i>N</i>-(Benzylidene)-<i>p</i>-toluenesulfinamide and Glycine Enolates
  作者：Franklin A. Davis、Jianghe Deng

  DOI：10.1021/ol048981y

  日期：2004.8.1

  Addition of differentially N-protected glycine enolates to enantiopure sulfinimines affords syn- and anti-alpha,beta-diamino esters with high diastereoselectivities and good yields.
• Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates
  作者：Teng Ai、Guigen Li

  DOI：10.1016/j.bmcl.2009.03.001

  日期：2009.7

  Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample. Published by Elsevier Ltd.