(4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester | 186817-91-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester
• 英文别名: (5beta)-3,7-Dioxo-4alpha-methyl-6beta-[(R)-1-(triethylsilyloxy)ethyl]-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-nitrobenzyl ester；(4-nitrophenyl)methyl (4R,5R,6S)-4-methyl-3,7-dioxo-6-[(1R)-1-triethylsilyloxyethyl]-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 186817-91-4
• 化学式: C₂₃H₃₂N₂O₇Si
• 分子量: 476.602
• InChiKey: LMRIYEYYHIFRFD-WZNCEAAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 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：

  (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-methyl-3-diazo-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl]azetidin-2-one 在 Rh₂(C₇H₁₅CO₂)4 咪唑 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4R,5R,6S)-4-methyl-3,7-dioxo-6-((1'R)-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl-ester
  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。
• 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。
• 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.
• [EN] FLUORESCENT CARBAPENEMS<br/>[FR] CARBAPÉNEMES FLUORESCENTS
  申请人：PFAENDLER HANS RUDOLF

  公开号：WO2012003955A4

  公开（公告）日：2012-03-08
• Practical Synthesis of Anti-Methicillin-Resistant <i>Staphylococcus</i> <i>Aureus</i> (MRSA) Carbapenem L-742,728
  作者：Nobuyoshi Yasuda、Mark A. Huffman、Guo-Jie Ho、Lyndon C. Xavier、Chunhua Yang、Khateeta M. Emerson、Fuh-Rong Tsay、Yulan Li、Michael H. Kress、Dale L. Rieger、Sandor Karady、Paul Sohar、Newton L. Abramson、Ann E. DeCamp、David J. Mathre、Alan W. Douglas、Ulf-H. Dolling、Edward J. J. Grabowski、Paul J. Reider

  DOI：10.1021/jo980381n

  日期：1998.8.1

  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.