(3R,4R)-1-(tert-butoxycarbonyl)-3-[(triethylsilyl)oxy]-3-methyl-4-thienyl-azetidin-2-one | 817201-66-4

• 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: (3R,4R)-1-(tert-butoxycarbonyl)-3-[(triethylsilyl)oxy]-3-methyl-4-thienyl-azetidin-2-one
• 英文别名: tert-butyl (3R,4R)-3-methyl-2-oxo-4-thiophen-2-yl-3-triethylsilyloxyazetidine-1-carboxylate
• CAS: 817201-66-4
• 化学式: C₁₉H₃₁NO₄SSi
• 分子量: 397.611
• InChiKey: NJDCNHPRIMLVFU-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  84.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-(tert-butoxycarbonyl)-3-[(triethylsilyl)oxy]-3-methyl-4-thienyl-azetidin-2-one 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-2-methyl-3-(2-thienyl)propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

  摘要：

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.

  DOI：

  10.1021/jo0486793
• 作为产物：
  描述：

  (3R,4R)-3-hydroxy-3-methyl-4-(thiophen-2-yl)azetidin-2-one 在 咪唑 、 4-二甲氨基吡啶 作用下， 生成 (3R,4R)-1-(tert-butoxycarbonyl)-3-[(triethylsilyl)oxy]-3-methyl-4-thienyl-azetidin-2-one
  参考文献：
  名称：

  Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle

  摘要：

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.

  DOI：

  10.1021/jo0486793

文献信息

• 2′-Methyl taxanes: synthesis and NMR configurational assignment
  作者：Paolo Dambruoso、Carla Bassarello、Giuseppe Bifulco、Giovanni Appendino、Arturo Battaglia、Andrea Guerrini、Gabriele Fontana、Luigi Gomez-Paloma

  DOI：10.1016/j.tetlet.2005.03.095

  日期：2005.5

  2′-methyl taxanes was developed. The issue of configurational assignment at the newly formed side-chain quaternary stereocenter was solved and put into a more general context by integrating information from an alternative diastereoselective synthesis of model compounds and from spectroscopic measurements, critically comparing the J-Based and the Universal NMR Database approaches.

  利用氧化烷基化方法，开发了非非对映选择性进入2'-甲基紫杉烷类的方法。通过整合来自模型化合物的替代非对映选择性合成和光谱测量的信息，严格地比较基于J的基团和通用NMR数据库，解决了新形成的侧链四元立体中心的构型分配问题并将其置于更一般的背景下方法。
• Synthesis of Optically Active Constrained 2-Substituted Norstatines:  A Straightforward Application of Seebach's “SRS” Synthetic Principle
  作者：Arturo Battaglia、Andrea Guerrini、Carlo Bertucci

  DOI：10.1021/jo0486793

  日期：2004.12.1

  A straightforward two-step methodology of synthesis of optically active (2,R)-substituted norstatines via addition of N-tert-butoxycarbonyl-substituted aldimines to (2S)-chiral enolates of 1,3-dioxolan-4-ones has been developed. In particular, the use of the natural (2S)-malic acid is examined for the synthesis of potential GABAergic spirocyclic gamma-lactams.