(5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester | 36273-78-6

• 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: (5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester
• 英文别名: benzyl 6α-methyl-6β-aminopenicillanate；benzyl (2S,5R,6R)-6-amino-3,3,6-trimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 36273-78-6
• 化学式: C₁₆H₂₀N₂O₃S
• 分子量: 320.412
• InChiKey: HMOLYQGRNFTQGL-SGIREYDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester 在 palladium on activated charcoal deacetoxy 、 deacetoxycephalosporin C synthase 、 deacetylcephalosporin C synthase 、 氢气 、 铁粉 、 碳酸氢钠 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 40.0h， 生成 (2R)-2-[(2R)-1-amino-2-[[(5R)-5-amino-5-carboxypentanoyl]amino]-1-oxopropan-2-yl]-5-formyl-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 N-氯-N-吡啶基乙酰肼 、 magnesium sulfate 、 对甲苯磺酸 、 苯基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 82.5h， 生成 (5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x

文献信息

• 6-Methyl penicillins
  申请人：Merck & Co., Inc.

  公开号：US04219462A1

  公开（公告）日：1980-08-26

  New 6-methyl penicillins and the corresponding 6-aminopenicillanic acid compounds and processes for the preparation of these penicillins are provided. The new penicillins are antibiotics which are active against various gram-negative and gram-positive pathogens.

  提供了新的6-甲基青霉素和相应的6-氨基青霉酸化合物以及制备这些青霉素的过程。这些新的青霉素是抗生素，对各种革兰氏阴性和革兰氏阳性病原体具有活性。
• Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0013617A1

  公开（公告）日：1980-07-23

  This invention relates to a process for the preparation of certain penicillin derivatives which are useful as β-lactamase inhibitors. The compounds which may be prepared by the process of this invention have formula (I), or a pharmaceutically acceptable salt or ester thereof: wherein R represents hydrogen, halogen, C1-6alkylthio, C1-6alkyl or alkyl substituted with phenyl, carboxy, C1-6alkoxycarbonyl, hydroxyorC1-6alkylthio, and n is zero, 1 or 2. In addition certain of the compounds produced by the process of the invention are novel compounds.

  本发明涉及一种制备某些青霉素衍生物的工艺，这些衍生物可用作β-内酰胺酶抑制剂。可通过本发明工艺制备的化合物具有式（I）或其药学上可接受的盐或酯： 其中R代表氢、卤素、C1-6烷硫基、C1-6烷基或被苯基、羧基、C1-6烷氧基羰基、羟基或C1-6烷硫基取代的烷基，n为0、1或2。此外，本发明工艺生产的某些化合物是新型化合物。
• Substituted penicillins and cephalosporins II. C-6(7)-alkyl derivatives (1)
  作者：Raymond A. Firestone、Natalie Schelechow、David B.R. Johnston、B.G. Christensen

  DOI：10.1016/s0040-4039(01)84328-8

  日期：1972.1
• Preparation of 6.beta.-imidopenicillinate 1(S)-oxides
  作者：Jack E. Baldwin、Stephen R. Herchen、Jon C. Clardy、K. Hirotsu、T. S. Chou

  DOI：10.1021/jo00401a012

  日期：1978.3
• US4219462A
  申请人：——

  公开号：US4219462A

  公开（公告）日：1980-08-26