cis-(3S,4S)-1-p-toluenesulfonyl-3-phenyl-4-ethoxycarbonylazetidinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: cis-(3S,4S)-1-p-toluenesulfonyl-3-phenyl-4-ethoxycarbonylazetidinone
• 英文别名: ethyl (2S,3S)-1-(4-methylphenyl)sulfonyl-4-oxo-3-phenylazetidine-2-carboxylate
• 化学式: C₁₉H₁₉NO₅S
• 分子量: 373.43
• InChiKey: SORFHLMNRUPFTR-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-(3S,4S)-1-p-toluenesulfonyl-3-phenyl-4-ethoxycarbonylazetidinone 在 [(n-C₆H₁₃)4N][2-(1-Bn-4,5-dihydro-1H-imidazol-2-yl)C₆H₄SO₃] 、 1,8-双二甲氨基萘 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 trans-1-(p-toluenesulfonyl)-3-phenyl-4-ethoxycarbonylazetidinone
  参考文献：
  名称：

  An Anionic Nucleophilic Catalyst System for the Diastereoselective Synthesis of trans-β-Lactams

  摘要：

  [GRAPHICS]Trans-disubstituted beta-lactams show increasing utility and prominence in numerous pharmaceutical applications, making their asymmetric synthesis an attractive goal for chemists. We introduce an anionic, nucleophilic catalyst system that provides an efficient, diastereoselective route to trans-disubstituted beta-lactams, a complement to our previously described catalytic methodology for generating the corresponding cis diastereomers. This catalytic, "switch mechanism" process allows for flexibility in the stereoselective synthesis of beta-lactams, producing either cis or trans products as desired from the same substrates.

  DOI：

  10.1021/ol0511070
• 作为产物：
  描述：

  (E)-ethyl 2-(tosylimino)acetate 、 苯乙酰氯 在 benzoylquinidine 、 1,8-双二甲氨基萘 作用下， 以 甲苯 为溶剂， 以64%的产率得到cis-(3S,4S)-1-p-toluenesulfonyl-3-phenyl-4-ethoxycarbonylazetidinone
  参考文献：
  名称：

  乙烯酮和亚胺的首次催化反应的发展：β-内酰胺的催化不对称合成

  摘要：

  我们报告了由乙烯酮（或其衍生的两性离子烯醇化物）和亚胺的催化反应的发展产生的 β-内酰胺的催化、不对称合成的实用方法。这些不对称反应的产物可以作为许多酶抑制剂和候选药物以及有价值的合成中间体的前体。我们详细研究了以质子海绵为化学计量基础的 β-内酰胺形成反应的机制，包括动力学和同位素标记研究。还提出了基于分子力学 (MM) 计算的立体化学模型，以解释在我们的反应中观察到的立体规则感应，并为其他催化剂系统的设计提供指导。

  DOI：

  10.1021/ja0258226

文献信息

• Bicarbonate Salts as Cost-Effective Bases for the Synthesis of Ketenes and Their Synthetic Equivalents Applied to the Asymmetric Synthesis of β-Lactams
  作者：Thomas Lectka、Meha H. Shah、Stefan France

  DOI：10.1055/s-2003-41497

  日期：——

  of bicarbonate salts as viable alternatives to more expensive bases for the in situ generation of ketenes and their synthetic equivalents. We have successfully applied this to the catalytic, asymmetric synthesis of β-lactams.

  我们报告了使用碳酸氢盐作为原位生成烯酮及其合成等价物的更昂贵碱的可行替代品。我们已成功地将其应用于 β-内酰胺的催化不对称合成。
• 一种制备手性β-内酰胺的方法
  申请人：江苏恒盛药业有限公司

  公开号：CN117603116A

  公开（公告）日：2024-02-27

  本发明公开了一种制备手性β‑内酰胺的方法，在干燥的反应瓶中加入有机溶剂和底物I，质子海绵，然后加入催化剂III和底物II，控制一定温度下保温反应经后处理得产物IV。本发明通过合适的手性催化剂，获得目标产物，该方法条件温和，手型选择性高。
• Asymmetric Catalysis on Sequentially-Linked Columns
  作者：Ahmed M. Hafez、Andrew E. Taggi、Travis Dudding、Thomas Lectka

  DOI：10.1021/ja016556j

  日期：2001.11.1

  We report a catalytic asymmetric reaction process that involves the use of solid-phase reagents and catalysts that constitute the packing of a series of "reaction columns". This process was applied to the catalytic asymmetric synthesis of beta -lactams, to yield pure products with excellent enantio- and diastereoselectivity. We have identified several advantages to conducting chemical reactions on sequential columns, including ease of catalyst and reagent recovery and simplified purification steps that preclude the need for chromatography.
• Molecular mechanics calculations as predictors of enantioselectivity for chiral nucleophile catalyzed reactions
  作者：Andrew E. Taggi、Ahmed M. Hafez、Travis Dudding、Thomas Lectka

  DOI：10.1016/s0040-4020(02)00987-0

  日期：2002.10

  We present molecular mechanics (MM) calculations as models of activated complexes for the beta-lactam forming [2+2] cycloaddition between imino ester 4 and the zwitterionic intermediates derived from ketenes and various chiral nucleophilic catalysts. Our method employs the use of Monte Carlo conformational searches utilizing the MMFF force field contained within the Macromodel program. These models accurately predict the sense of stereochemical induction observed experimentally. Also, the predicted energetic differences for minima leading to (R) or (S)-derived ketene facial selectivity correlate in a general sense with the magnitude of the enantioselectivity. This work establishes that our approach represents a viable method for the design of new nucleophilic catalysts a priori using MM calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.