(4-nitrophenyl)methyl (4R)-2-diazo-3-oxo-4-[(2R,3S)-4-oxo-3-[(1R)-1-triethylsilyloxyethyl]azetidin-2-yl]pentanoate | 186817-88-9

• 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: (4-nitrophenyl)methyl (4R)-2-diazo-3-oxo-4-[(2R,3S)-4-oxo-3-[(1R)-1-triethylsilyloxyethyl]azetidin-2-yl]pentanoate
• CAS: 186817-88-9
• 化学式: C₂₃H₃₂N₄O₇Si
• 分子量: 504.615
• InChiKey: CPQDAVLAIXKRHN-OHDICMOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)methyl (4R)-2-diazo-3-oxo-4-[(2R,3S)-4-oxo-3-[(1R)-1-triethylsilyloxyethyl]azetidin-2-yl]pentanoate 在 Rh₂(C₇H₁₅CO₂)4 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 、 zinc dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成 [4S-(4α,5β,6β(S*))]-1-(2-amino-2-oxoethyl)-({6-[4-methyl-2-({[(4-nitrophenyl)methyl]oxy}carbonyl)-7-oxo-6-{1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-en-3-yl]-9-oxo-9H-fluoren-2-yl}methyl)-1,4-diazaniabicyclo[2.2.2]octane 1-propanesulp...
  参考文献：
  名称：

  Practical Synthesis of Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Carbapenem L-742,728

  摘要：

  Ani-MRSA carbapenem, L-742,728, has been prepared in large quantity using, the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

  DOI：

  10.1021/jo980381n
• 作为产物：
  描述：

  三乙基氯硅烷 、 (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-methyl-3-diazo-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]azetidin-2-one 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 生成 (4-nitrophenyl)methyl (4R)-2-diazo-3-oxo-4-[(2R,3S)-4-oxo-3-[(1R)-1-triethylsilyloxyethyl]azetidin-2-yl]pentanoate
  参考文献：
  名称：

  Synthesis of an Anti-Methicillin-Resistant Staphylococcus aureus (MRSA) Carbapenem via Stannatrane-Mediated Stille Coupling

  摘要：

  A short synthesis of carbapenem 1 is described. The key step involves the cross-coupling of an enol triflate with an amino-substituted sp(3) carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.

  DOI：

  10.1021/ol005641d

文献信息

• Crystalline 2-hydroxymethyl carbapenem intermediate compounds and process for synthesis thereof
  申请人：Merck & Co., Inc.

  公开号：US06346617B1

  公开（公告）日：2002-02-12

  A process for preparation of a compound of formula I: wherein: R1 represents CH3 or H; and P represents a protecting group; comprising reacting a compound of formula IV:  wherein R1 and P and are defined above and R4 represents triflate or SO2F; in the presence of a catalyst and (R3)3SnCH2OP″, wherein each R3 represents C1-4 lower alkyl, and P″ represents H or a protecting group, to yield the compound of formula I.

  一种制备公式I化合物的方法，其中：R1代表CH3或H; P代表保护基; 包括在催化剂和(R3)3SnCH2OP"的存在下，将公式IV化合物与R4代表三氟甲烷磺酸酯或SO2F的化合物反应，其中R1和P如上所定义，R4代表三氟甲烷磺酸酯或SO2F，以生成公式I化合物。其中，每个R3代表C1-4低烷基，P"代表H或保护基。