(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-methyl-allyl)-azetidin-2-one | 403609-97-2

• 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: (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-methyl-allyl)-azetidin-2-one
• 英文别名: (3S,4R)-4-[(2S)-but-3-en-2-yl]-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one
• CAS: 403609-97-2
• 化学式: C₂₁H₄₃NO₂Si₂
• 分子量: 397.749
• InChiKey: PVGPHJUTZMINEL-BSDSXHPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-methyl-allyl)-azetidin-2-one 在 氧气 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3S,4R)-4-[(Z,S)-3-iodo-3-ethoxycarbonyl-1-methylprop-2-enyl]-1-(tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-2-azetidinone
  参考文献：
  名称：

  Synthesis of 3-Alkoxycarbonyl-1β-methylcarbapenem by Using the Palladium-Catalyzed C−N Bond-Forming Reaction between Vinyl Halide and β-Lactam Nitrogen

  摘要：

  3-Alkoxycarbonyl-1beta-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and beta-lactam nitrogen. In this reaction, the use of Pd(OAc)(2) and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)(2) in the absence of a base is necessary to increase the yield.

  DOI：

  10.1021/jo020584i
• 作为产物：
  描述：

  (3S,4R)-4-but-3-en-2-yl-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one 生成 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-1-methyl-allyl)-azetidin-2-one 、 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-methyl-allyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis of 3-Alkoxycarbonyl-1β-methylcarbapenem by Using the Palladium-Catalyzed C−N Bond-Forming Reaction between Vinyl Halide and β-Lactam Nitrogen

  摘要：

  3-Alkoxycarbonyl-1beta-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and beta-lactam nitrogen. In this reaction, the use of Pd(OAc)(2) and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)(2) in the absence of a base is necessary to increase the yield.

  DOI：

  10.1021/jo020584i

文献信息

• Synthesis of 3-alkoxycarbonyl-1β-methylcarbapenem using palladium-catalyzed amidation of vinyl halide
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1016/s0040-4039(01)02091-3

  日期：2002.1

  3-Alkoxycarbonyl-1β-methylcarbapenem could be synthesized using a palladium-catalyzed CN bond-forming reaction. In this reaction, the use of Pd(OAc)2 and DPEphos gave a good result, and generation of Pd(0) in the absence of a base is necessary to increase the yield.

  可以通过钯催化的C bondN键形成反应合成3-烷氧羰基-1β-甲基咔啉。在该反应中，使用Pd（OAc）2和DPEphos可获得良好的结果，并且在不存在碱的情况下生成Pd（0）对于提高产率是必需的。
• Novel Synthesis of Carbapenam by Intramolecular Attack of Lactam Nitrogen toward η¹-Allenyl and η³-Propargylpalladium Complex
  作者：Yuji Kozawa、Miwako Mori

  DOI：10.1021/jo030123c

  日期：2003.10.1

  When a THF solution of beta-lactam having propargyl phosphate was warmed in the presence of 5 mol % of Pd-2(dba)(3).CHCl3, 20 mol % of a bidentate ligand, and sodium acetate (1.5 equiv) at 40 degreesC for 22 h, carbapenam was produced in high yield. In this reaction, the lactam nitrogen attacked the central carbon of a eta(3)-propargylpalladium complex, which was formed from propargyl phosphate and Pd(0).