4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate | 165817-82-3

• 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-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate
• 英文别名: (4-nitrophenyl)methyl (4R,5R,6S)-4-methyl-7-oxo-6-[(1R)-1-triethylsilyloxyethyl]-3-(trifluoromethylsulfonyloxy)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 165817-82-3
• 化学式: C₂₄H₃₁F₃N₂O₉SSi
• 分子量: 608.665
• InChiKey: CBVMPTLCHSAMCU-OHDICMOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate 在 potassium phthalate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (4-nitrophenyl)methyl (4S,5R,6S)-3-[7-(hydroxymethyl)-9-oxofluoren-3-yl]-4-methyl-7-oxo-6-[(1R)-1-triethylsilyloxyethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  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：

  4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate 在 三乙胺 作用下， 反应 1.5h， 生成 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate
  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

文献信息

• FLUORESCENT CARBAPENEMS
  申请人：Pfaendler Hans Rudolf

  公开号：US20130102017A1

  公开（公告）日：2013-04-25

  Chromogenic or fluorescent carbapenems according to formula I, wherein Ar is a mono or disubstituted carbocyclic aromatic group or an optionally mono or disubstituted heterocyclic aromatic group, are useful compounds for the detection of bacterial carbapenemase.

  根据公式I，具有发色或荧光的碳青霉烯化合物，其中Ar是单取代或双取代的碳环芳基团或可选的单取代或双取代的杂环芳基团，可用于检测细菌碳青霉烯酶的有用化合物。
• The syntheses of functionalized 2-alkenyl and alkynyl-1-β-methyl-carbapenems via the stille cross-coupling reaction
  作者：Kevin D. Dykstra、Frank DiNinno

  DOI：10.1016/s0040-4039(98)00121-x

  日期：1998.4

  The Stille cross-coupling reaction is an extremely mild and versatile method for the coupling of organostannanes with vinyl triflates. This methodology has been extended to include functionalized 2-alkenyl and alkynyl-1-β-methylcarbapenems.

  Stille交叉偶联反应是一种非常温和且通用的方法，用于将有机锡烷与乙烯基三氟甲磺酸酯偶联。该方法已经扩展到包括功能化的2-烯基和炔基-1-β-甲基卡巴南。
• 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。
• Synthesis of an Anti-Methicillin-Resistant <i>Staphylococcus aureus </i>(MRSA) Carbapenem via Stannatrane-Mediated Stille Coupling
  作者：Mark S. Jensen、Chunhua Yang、Yi Hsiao、Nelo Rivera、Kenneth M. Wells、John Y. L. Chung、Nobuyoshi Yasuda、David L. Hughes、Paul J. Reider

  DOI：10.1021/ol005641d

  日期：2000.4.1

  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.
• Preparation of crystallinep-nitrobenzyl 2-hydroxymethyl carbapenem as a key intermediate for the anti-MRS carbapenem L-786,392
  作者：Nobuyoshi Yasuda、Chunhua Yang、Kenneth M. Wells、Mark S. Jensen、David L. Hughes

  DOI：10.1016/s0040-4039(98)02393-4

  日期：1999.1

  Crystalline p-nitrobenzyl esters of 2-hydroxymethyl carbapenem derivatives were prepared in one pot from the corresponding diazo compounds and Bu3SnCH2OH. The TES protected 2-hydroxymethyl carbapenem was successfully converted to an anti-MRS carbapenem L-786,392. (C) 1998 Elsevier Science Ltd. All rights reserved.