6-t-butoxycarbonylaminopenicillanic acid | 26531-14-6

• 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: 6-t-butoxycarbonylaminopenicillanic acid
• 英文别名: (2S,5R,6R)-6-(tert-butoxycarbonylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid；6-Butyloxycarbonylamino-penicillansaeure；6-Boc-aminopenicillanic acid；6β-tert-butoxycarbonylamino-penicillanic acid；(2S,5R,6R)-6-{[(tert-butoxy)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid；(2S,5R,6R)-3,3-dimethyl-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 26531-14-6
• 化学式: C₁₃H₂₀N₂O₅S
• 分子量: 316.378
• InChiKey: UYTQFXINTFNFHJ-BKPPORCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-t-butoxycarbonylaminopenicillanic acid 在 镍 氢气 、 碳酸氢钠 、 diborane(6) 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 8.28h， 生成 benzhydryl (2'S,2R)-2-<(2'-t-butoxycarbonylamino-3'-hydroxy)propylamino>-3-methylbutanoate
  参考文献：
  名称：

  Sammes, Peter G.; Smith, Steven, Journal of the Chemical Society. Perkin transactions I, 1984, p. 2415 - 2420

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氨基青霉烷酸 、 氟甲酸叔丁酯 生成 6-t-butoxycarbonylaminopenicillanic acid
  参考文献：
  名称：

  青霉素向头孢菌素的转化

  摘要：

  AbstractA new method for the degradation of the thiazolidine ring in penicillins is described. Penicillin V (8a), penicillin G (8b) and 6‐t‐butoxycarbonylaminopenicillanic acid (33) (BOC‐6‐APA) were converted via their acylazides and isocyanates (10 and 34) into 2,2,2‐trichloroethyl urethanes (11 and 35). Reductive removal of the trichloroethoxycarbonyl groups in an aqueous medium gave the 3‐hydroxy‐penam‐derivatives 13 and 36. The structure and various reactions of these carbinolamides are discussed in detail. An oxidative radical fragmentation (using lead tetraacylates and light) followed by thermal treatment transformed the 3‐hydroxy‐penam‐derivatives into the N‐formyl‐β‐lactam‐thio‐enolethers 27 and 37 in which the formyl group could be replaced by hydrogen. Reactions of the β‐lactam and thio‐enolether functions are described.The BOC‐derivative 37 can be transformed into the isomeric compound 3, an intermediate in Woodward's total synthesis of cephalosporins.

  DOI：

  10.1002/hlca.19720550209

文献信息

• Chemoselective Cross-Coupling of <i>gem</i>-Borazirconocene Alkanes with Aryl Halides
  作者：Chao Yang、Yadong Gao、Songlin Bai、Chao Jiang、Xiangbing Qi

  DOI：10.1021/jacs.0c03821

  日期：2020.7.1

  chemoselective conversion of the carbon-metal bond of gem-dimetallic reagents enables rapid and sequential formation of multiple carbon-carbon and carbon-heteroatom bonds, thus representing a powerful method for efficiently increasing structural complexity. Herein, we report a visible-light-induced, single nickel-catalyzed, chemoselective cross-coupling reaction between gem-borazirconocene alkanes and diverse

  宝石-双金属试剂的碳-金属键的直接和化学选择性转化能够快速、连续地形成多个碳-碳和碳-杂原子键，从而代表了一种有效增加结构复杂性的有效方法。在此，我们报告了一种可见光诱导的、单镍催化的、化学选择性交叉偶联的宝石-硼锆茂烷烃和多种芳基卤化物，以高产率提供了范围广泛的烷基 Bpin 衍生物，并具有出色的区域选择性。这种实用的方法具有非常简单的反应条件和广泛的底物范围。此外，我们系统地研究了 Bpin 导向的链行走过程，该过程是烷基二茂锆区域选择性的基础，从而揭示了用我们的方法实现的内烯烃远程官能化的机制。最后，DFT 计算表明该反应的高区域选择性源于 Bpin 基团的导向作用。
• β-内酰胺类衍生物、其制备方法和用途、以及其中间体和中间体的制备方法
  申请人：艾奇西（宜兴）新药研发有限公司

  公开号：CN112480143B

  公开（公告）日：2023-05-02

  本发明涉及新的式(I)的β‑内酰胺类衍生物，及其立体异构体、溶剂合物和可药用盐或酯，其中基团R1和R2具有说明书中所述的含义；还涉及所述化合物的制备方法、其作为抗微生物剂的用途、其中间体以及中间体的制备方法；此外，还涉及含有本发明的化合物的药物组合物及其用途。
• [EN] SYNTHESIS PROCESS OF PRECURSORS OF DERIVATIVES OF β-LACTAM NUCLEI AND PRECURSORS AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE PRÉCURSEURS DE DÉRIVÉS DE NOYAU Β-LACTAME ET PRÉCURSEURS ET DÉRIVÉS DE CEUX-CI
  申请人：BONOMI PAOLO

  公开号：WO2017153892A1

  公开（公告）日：2017-09-14

  A synthesis process of precursors of derivatives of beta-lactam compounds, said beta-lactam compounds being selected from 6-aminopenicillanic acid and 7-aminocephalosporanic acid, preferably 6-aminopenicillanic acid, comprising the following steps: a) protection of the amine group of the beta-lactam compound, selected from 6-aminopenicillanic acid and 7-aminocephalosporanic acid, preferably 6-aminopenicillanic acid, through the formation of a carbamate by reaction with a dicarbonate; b) esterification of the carboxyl group in position 2 of the beta-lactam compound obtained in step a) by reaction with propargyl alcohol.

  一种合成β-内酰胺化合物衍生物前体的过程，所述β-内酰胺化合物被选择自6-氨基青霉酸和7-氨基头霉素酸，优选6-氨基青霉酸，包括以下步骤：a) 通过与二碳酸酯反应形成碳酸酯来保护所选β-内酰胺化合物的胺基，所选β-内酰胺化合物为6-氨基青霉酸和7-氨基头霉素酸，优选6-氨基青霉酸；b) 通过与丙炔醇反应酯化所得步骤a)中β-内酰胺化合物的2位羧基。
• Design, synthesis and antiviral efficacy of a series of potent chloropyridyl ester-derived SARS-CoV 3CLpro inhibitors
  作者：Arun K. Ghosh、Gangli Gong、Valerie Grum-Tokars、Debbie C. Mulhearn、Susan C. Baker、Melissa Coughlin、Bellur S. Prabhakar、Katrina Sleeman、Michael E. Johnson、Andrew D. Mesecar

  DOI：10.1016/j.bmcl.2008.08.082

  日期：2008.10

  Design, synthesis and biological evaluation of a series of 5-chloropyridine ester-derived severe acute respiratory syndrome-coronavirus chymotrypsin-like protease inhibitors is described. Position of the carboxylate functionality is critical to potency. Inhibitor 10 with a 5-chloropyridinyl ester at position 4 of the indole ring is the most potent inhibitor with a SARS-CoV 3CLpro IC(50) value of 30

  描述了一系列5-氯吡啶酯衍生的严重急性呼吸综合征-冠状病毒糜蛋白酶样蛋白酶抑制剂的设计、合成和生物学评价。羧酸酯官能团的位置对于效力至关重要。吲哚环 4 位具有 5-氯吡啶酯的抑制剂 10 是最有效的抑制剂，其 SARS-CoV 3CLpro IC(50) 值为 30 nM，抗病毒 EC(50) 值为 6.9 microM。分子对接研究提供了这些抑制剂可能的结合模式。
• Die Umwandlung von Penicillinen in Cephalosporine. Modifikationen von Antibiotika, 3. Mitteilung
  作者：K. Heusler

  DOI：10.1002/hlca.19720550209

  日期：1972.1.31

  AbstractA new method for the degradation of the thiazolidine ring in penicillins is described. Penicillin V (8a), penicillin G (8b) and 6‐t‐butoxycarbonylaminopenicillanic acid (33) (BOC‐6‐APA) were converted via their acylazides and isocyanates (10 and 34) into 2,2,2‐trichloroethyl urethanes (11 and 35). Reductive removal of the trichloroethoxycarbonyl groups in an aqueous medium gave the 3‐hydroxy‐penam‐derivatives 13 and 36. The structure and various reactions of these carbinolamides are discussed in detail. An oxidative radical fragmentation (using lead tetraacylates and light) followed by thermal treatment transformed the 3‐hydroxy‐penam‐derivatives into the N‐formyl‐β‐lactam‐thio‐enolethers 27 and 37 in which the formyl group could be replaced by hydrogen. Reactions of the β‐lactam and thio‐enolether functions are described.The BOC‐derivative 37 can be transformed into the isomeric compound 3, an intermediate in Woodward's total synthesis of cephalosporins.