(2S,3R)-3-Methylaziridine-2-carboxylate | 191993-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2S,3R)-3-Methylaziridine-2-carboxylate
• 英文别名: (2S,3R)-methyl 3-methyl-1-tritylaziridine-2-carboxylate；methyl (2S,3R)-3-methyl-1-tritylaziridine-2-carboxylate
• CAS: 191993-86-9
• 化学式: C₂₄H₂₃NO₂
• 分子量: 357.452
• InChiKey: BVGNONFOZJRWNA-IIAXJLLOSA-N

物化性质

• 沸点：
  437.9±45.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Methylaziridine-2-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (2S,3R)-1-tert-butyl 2-methyl 3-methylaziridine-1,2-dicarboxylate
  参考文献：
  名称：

  Hepatitis C Virus Inhibitors

  摘要：

  揭示了具有一般公式（I）的丙型肝炎病毒抑制剂。还公开了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。

  公开号：

  US20150284409A1
• 作为产物：
  描述：

  (2S,3S)-methyl 3-hydroxy-2-(tritylamino)butanoate 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (2S,3R)-3-Methylaziridine-2-carboxylate
  参考文献：
  名称：

  Hepatitis C Virus Inhibitors

  摘要：

  揭示了具有一般公式（I）的丙型肝炎病毒抑制剂。还公开了包含这些化合物的组合物以及使用这些化合物抑制HCV的方法。

  公开号：

  US20150284409A1

文献信息

• Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives
  作者：Christophe Dugave、André Ménez

  DOI：10.1016/s0957-4166(97)00109-2

  日期：1997.5

  This strategy was applied to the synthesis of lanthionines, the monosulfide analogs of cystine. Orthogonally protected sulfide adducts from L- and D-cysteines, threo-β-methyl-L-cysteine and D-penicillamine were isolated in 81–88% yield (ee>98%). This strategy was applied to the prepration of lanthionine and cyclolanthionine suitably protected for peptide synthesis.

  衍生自亲电子的反应性Ñ -tritylserine，苏氨酸和异基因朝向选择的亲核试剂的苏氨酸酯进行了研究。用N-三苯并碘丙氨酸和软亲核试剂（例如硫醇）可获得替代产品的最佳收率。该策略被用于合成胱氨酸的单硫醚类似物羊毛硫氨酸。从L-和d-半胱氨酸，正交保护的加合物硫化物苏- β -甲基-L-半胱氨酸和d青霉胺在81-88％的产率（ee值> 98％）中分离得到。将该策略应用于适当保护用于肽合成的羊毛硫氨酸和环羊毛硫氨酸的制备。
• A convenient method of preparing optically active (S)-N-tritylaziridine-2-carboxylate esters from (S)-β-haloamino acids
  作者：Yasuo Kato、Kenji Fukumoto

  DOI：10.1039/a909140h

  日期：——

  A convenient method of preparing optically active (S)-N-tritylaziridine-2-carboxylate esters via intramolecular cyclization of (S)-N-trityl-β-haloamino acid esters is described.

  描述了一种通过 (S)-N-三苯甲基-β-卤代氨基酸酯的分子内环化制备光学活性 (S)-N-trititylaziridine-2-羧酸酯的简便方法。
• Total Synthesis and Structure Assignment of Papuamide B, A Potent Marine Cyclodepsipeptide with Anti-HIV Properties
  作者：Weiqing Xie、Derong Ding、Weiwei Zi、Guangyu Li、Dawei Ma

  DOI：10.1002/anie.200705557

  日期：2008.3.31
• An experimental and theoretical study on free ligand conformational preferences and enantioselectivity relationship for the asymmetric addition of diethylzinc to benzaldehyde
  作者：Min-Can Wang、Zhi-kang Liu、Song Li、Xue Ding、Yuan Li、Ming-Sheng Tang

  DOI：10.1016/j.tetasy.2010.03.009

  日期：2010.3

  An experimental and theoretical study on free ligand conformational preferences and enantioselectivity relationship has been described for the asymmetric addition of diethylzinc to benzaldehyde. The results show that a correlation must exist between the ground-state ligand conformational populations and the observed ee values in this reaction. As the populations of the free ligand conformation (the desired conformation) in favor of the improvement of the reaction enantioselectivity increase, so does the reaction enantioselectivity. However, the desired conformation must not be the preferred one of the ground-state ligand. This conformation-enantioselectivity relationship is well explained based on a zinc amino-alkoxide (a true asymmetric catalyst). The final synthesis and assessment of the new chiral catalyst in the asymmetric addition of Et2Zn to benzaldehyde revealed that this necessary relationship guided our design of highly enantioselective ligands or rational improvement of existing ligands by means of knowledge of conformational analysis. (C) 2010 Elsevier Ltd. All rights reserved.
• HEPATITIS C VIRUS INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2914613A1

  公开（公告）日：2015-09-09