(2-tert-Butoxycarbonylamino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester | 186091-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-tert-Butoxycarbonylamino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester
• 英文别名: ethyl (2Z)-2-hydroxyimino-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]acetate
• CAS: 186091-52-1
• 化学式: C₁₂H₁₇N₃O₅S
• 分子量: 315.35
• InChiKey: XQQIJAAFFPLUAY-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2-tert-Butoxycarbonylamino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester 在 吡啶 、 sodium hydroxide 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (6R,7R)-3-Acetylsulfanyl-7-{2-(2-tert-butoxycarbonylamino-thiazol-4-yl)-2-[(Z)-trityloxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens

  摘要：

  The variety of cephalosporins 1 and 2 which possessed C(3)-aminopyrimidinyl substituents were prepared and evaluated for their antibacterial activities. They exhibited excellent in vitro activities especially against respiratory tract pathogens such as penicillin resistant Streptococus pneumonia, Moraxella catarrhalis and Haemophilus influenza. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00425-x
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (2-Amino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester; hydrochloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (2-tert-Butoxycarbonylamino-thiazol-4-yl)-[(Z)-hydroxyimino]-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens

  摘要：

  The variety of cephalosporins 1 and 2 which possessed C(3)-aminopyrimidinyl substituents were prepared and evaluated for their antibacterial activities. They exhibited excellent in vitro activities especially against respiratory tract pathogens such as penicillin resistant Streptococus pneumonia, Moraxella catarrhalis and Haemophilus influenza. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00425-x

文献信息

• Practical Synthesis of Triethylammonium (<i>Z</i>)-2-[2-(Boc-amino)thiazol-4-yl]-2-(trityloxyimino)acetate, the Side Chain of Cefmatilen
  作者：Yoshihisa Goto、Yoshiyuki Masui、Yoji Kitaura、Tatsuya Kobayashi、Hisanori Takahashi、Akira Okuyama

  DOI：10.1021/op049804f

  日期：2005.1.1

  A practical synthesis of triethylammonium (Z)-2-[2-(N-tert-butoxycarbonylamino)thiazol-4-yl]-2-(triphenylmethyloxyimino)acetate (1) which is the C-7 side chain of cefmatilen, a new cephalosporin antibiotic, is described. The conditions were optimized to control the impurity and to increase the yield. Selective acetylation of oxime group before tert-butoxycarbonylation reduced the amount of Boc2O. Compound

  三乙基铵的实用合成（ż）-2- [2-（Ñ -叔丁氧羰基）噻唑-4-基] -2-（triphenylmethyloxyimino）乙酸甲酯（1），这是cefmatilen的C-7侧链，一个新的描述了头孢菌素抗生素。优化条件以控制杂质并提高产率。叔丁氧基羰基化之前肟基团的选择性乙酰化减少了Boc 2 O的量。通过这种改进的方法，由化合物6合成的化合物1的总产率为80％（比药用过程的产率高12％），并通过四反应序列进行合成。 （每个反应95％）。
• JPH09208568A
  申请人：——

  公开号：JPH09208568A

  公开（公告）日：1997-08-12
• Synthesis and antibacterial activities of novel C(3)-aminopyrimidinyl substituted cephalosporins including against respiratory tract pathogens
  作者：Chang-Seok Lee、Eun-Jung Ryu、Seong Ho Oh、Kyoung-Sook Paek、Mu Yong Kim、Hasik Youn

  DOI：10.1016/s0960-894x(00)00425-x

  日期：2000.9

  The variety of cephalosporins 1 and 2 which possessed C(3)-aminopyrimidinyl substituents were prepared and evaluated for their antibacterial activities. They exhibited excellent in vitro activities especially against respiratory tract pathogens such as penicillin resistant Streptococus pneumonia, Moraxella catarrhalis and Haemophilus influenza. (C) 2000 Elsevier Science Ltd. All rights reserved.