(6R)-3-acetoxymethyl-7c-hydroxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester | 63599-58-6

• 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: (6R)-3-acetoxymethyl-7c-hydroxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• 英文别名: 7α-hydroxy-cephalosporanic acid tert-butyl ester；7β-hydroxycephalosporanic acid t-butyl ester；t-butyl 7β-hydroxycephalosporanate；tert-butyl (6R,7S)-3-(acetyloxymethyl)-7-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 63599-58-6
• 化学式: C₁₄H₁₉NO₆S
• 分子量: 329.374
• InChiKey: HRKXVFGJOVBMKD-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R)-3-acetoxymethyl-7c-hydroxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-Acetoxymethyl-7-formyloxy-5,5,8-trioxo-5lambda*6*-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028
• 作为产物：
  描述：

  7-Aminocephalosporanic acid t-butyl ester 在 高氯酸 、 硫酸 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (6R)-3-acetoxymethyl-7c-hydroxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters

  摘要：

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.

  DOI：

  10.1021/jm00171a028

文献信息

• Process for preparing 7-oxo cephalosporins and 6-oxo penicillins
  申请人：SmithKline Corporation

  公开号：US04053468A1

  公开（公告）日：1977-10-11

  A process for preparing 7-oxo cephalosporins and 6-oxo penicillins by reaction of a 7-amino cephalosporin or 6-amino penicillin with a carbonyl-containing oxidizing agent is disclosed.

  公开了一种通过将7-氨基头孢菌素或6-氨基青霉素与含有羰基的氧化剂反应制备7-羟基头孢菌素和6-羟基青霉素的方法。
• Studies in .beta.-lactams. 6. Synthesis of substituted .beta.-lactams by addition of nitromethane to 6-oxopenicillanates and 7-oxocephalosporanates
  作者：Srinivasan Chandrasekaran、Arthur F. Kluge、John A. Edwards

  DOI：10.1021/jo00444a046

  日期：1977.11
• DOHERTY, JAMES B.;FINKE, PAUL E.;FIRESTONE, RAYMOND A.;SHAH, SHRENIK S.;T+
  作者：DOHERTY, JAMES B.、FINKE, PAUL E.、FIRESTONE, RAYMOND A.、SHAH, SHRENIK S.、T+

  DOI：——

  日期：——
• Inhibition of human leukocyte elastase. 1. Inhibition by C-7-substituted cephalosporin tert-butyl esters
  作者：James B. Doherty、Bonnie M. Ashe、Peter L. Barker、Thomas J. Blacklock、John W. Butcher、Gilbert O. Chandler、M. Ellen Dahlgren、Philip Davies、Conrad P. Dorn

  DOI：10.1021/jm00171a028

  日期：1990.9

  Time-dependent inhibitors of the enzyme human leukocyte elastase have been developed based on the cephem nucleus. A series of cephalosporin tert-butyl esters has been examined, and the activity of these compounds has been found to be very sensitive to C-7 substituents, with small, alpha-oriented, electron-withdrawing groups showing greatest activity. Additionally, the oxidation state of the sulfur atom has been found to play a role in potency, with sulfones showing considerably greater activity than the corresponding sulfides or beta-sulfoxides. The alpha-sulfoxides were inactive.