(R,E)-ethyl 2-[(tert-butylsulfinyl)imino]propanoate | 1289643-01-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (R,E)-ethyl 2-[(tert-butylsulfinyl)imino]propanoate
• 英文别名: ethyl (R,E)-2-((tert-butylsulfinyl)imino)propanoate；ethyl (2E)-2-[(R)-tert-butylsulfinyl]iminopropanoate
• CAS: 1289643-01-1
• 化学式: C₉H₁₇NO₃S
• 分子量: 219.305
• InChiKey: SWHXQAAHLOQPOZ-DNGMOHDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,E)-ethyl 2-[(tert-butylsulfinyl)imino]propanoate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以88%的产率得到ethyl 2-((R)-1,1-dimethylethylsulfinamido)propanoate
  参考文献：
  名称：

  Asymmetric Synthesis of α-Amino Acids by Reduction of N-tert-Butanesulfinyl Ketimine Esters

  摘要：

  A highly regio- and diastereoselective reduction of various N-tert-butanesulfinyl ketimine esters with L-Selectride resulting in the formation of alpha-amino acids is reported. This method is quite general and also practical for the preparation of both enantiomers of aryl or aliphatic a-amino acids in high yields.

  DOI：

  10.1021/jo200401a
• 作为产物：
  描述：

  丙酮酸乙酯 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到(R,E)-ethyl 2-[(tert-butylsulfinyl)imino]propanoate
  参考文献：
  名称：

  Asymmetric Synthesis of α-Amino Acids by Reduction of N-tert-Butanesulfinyl Ketimine Esters

  摘要：

  A highly regio- and diastereoselective reduction of various N-tert-butanesulfinyl ketimine esters with L-Selectride resulting in the formation of alpha-amino acids is reported. This method is quite general and also practical for the preparation of both enantiomers of aryl or aliphatic a-amino acids in high yields.

  DOI：

  10.1021/jo200401a

文献信息

• Stereochemical Assignment of the Protein-Protein Interaction Inhibitor JBIR-22 by Total Synthesis
  作者：Alan R. Healy、Miho Izumikawa、Alexandra M. Z. Slawin、Kazuo Shin-ya、Nicholas J. Westwood

  DOI：10.1002/anie.201411141

  日期：2015.3.23

  activity associated with a subfamily of the tetramic acid class of natural products. Despite the fact that members of this subfamily act as protein–protein interaction inhibitors that are of relevance to proteasome assembly, no synthetic work has been reported. This may be due to the fact that this subfamily contains an unnatural 4,4‐disubstitued glutamic acid, the synthesis of which provides a key challenge

  最近的报告强调了与特特拉姆酸类天然产物的一个亚科相关的生物活性。尽管该亚家族的成员充当与蛋白酶体组装相关的蛋白质-蛋白质相互作用抑制剂，但尚未报道合成工作。这可能是因为该亚家族含有非天然的 4,4-二取代谷氨酸，其合成提出了关键挑战。这种非天然氨基酸的掩蔽形式的高度立体选择性途径现在能够合成 JBIR-22 的两种可能的非对映体，并允许指定其相对和绝对立体化学。
• Asymmetric Synthesis of α-Amino Acids by Reduction of <i>N</i>-<i>tert</i>-Butanesulfinyl Ketimine Esters
  作者：Leleti Rajender Reddy、Aditya P. Gupta、Yugang Liu

  DOI：10.1021/jo200401a

  日期：2011.5.6

  A highly regio- and diastereoselective reduction of various N-tert-butanesulfinyl ketimine esters with L-Selectride resulting in the formation of alpha-amino acids is reported. This method is quite general and also practical for the preparation of both enantiomers of aryl or aliphatic a-amino acids in high yields.