tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate | 442154-65-6

• 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: tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate
• 英文别名: tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl) silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate；tert-butyl 3-[2-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]acetyl]benzoate
• CAS: 442154-65-6
• 化学式: C₂₄H₃₇NO₅Si
• 分子量: 447.647
• InChiKey: WYIUSLTVUDFVLB-XFQXTVEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl 3-{[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)-4-oxo-2-azetidinyl]acetyl}benzoate 在 四丁基氟化铵 、 溶剂黄146 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 tert-butyl 3-({(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxo-2-azetidinyl}acetyl)benzoate
  参考文献：
  名称：

  Novel carbapenem, medical and antibacterial comprisisng the same, and uses thereof

  摘要：

  公开号：

  EP1357123B8

文献信息

• Novel carbapenem compounds
  申请人：——

  公开号：US20040063683A1

  公开（公告）日：2004-04-01

  Carbapenem compounds having a substituted phenyl or a substituted thienyl directly attached to the 3-position of carbapenem nucleus as represented by the formula: 1 wherein Ring E is benzene ring or thiophene ring; R 1 is optionally OH-substituted C 1-3 alkyl; R 2 and R 3 represent each H, optionally substituted lower alkyl, etc.; R is H, or a group which is hydrolyzed in the living body to regenerate a carboxyl group, etc.; X is O or S; and Y represents H, lower alkyl, etc., or pharmaceutically acceptable salts thereof and medicaments containing said compound as the active ingredient. These compounds exhibit an excellent antibacterial activity over a broad range of Gram-positive and Gram-negative bacteria, in particular, penicillin-resistant Staphylococcus pneumoniae (PRSP) which has been isolated at an elevated frequency in recent years and thus causes a serious clinical problem, and Haemophilus influenzae which has acquired resistance against the existing &bgr;-lactam antibiotics over a wide scope due to penicillin-binding protein (PBP) mutations such as &bgr;-lactamase non-producing ampicillin-resistant (BLNAR) Haemophilus influenzae.

  具有取代苯基或取代噻吩基直接连接到碳青霉烯核的碳青霉烯化合物，如下式所示：1其中环E为苯环或噻吩环；R1是可选的OH取代的C1-3烷基；R2和R3分别表示H、可选取代的较低烷基等；R为H，或是在生物体内水解为羧基等的基团；X为O或S；Y表示H、较低烷基等，或其药学上可接受的盐，以及含有该化合物作为活性成分的药物。这些化合物表现出优异的抗菌活性，对广泛的革兰氏阳性和革兰氏阴性细菌具有杀菌作用，特别是对近年来分离频率升高并引起严重临床问题的青霉素耐药性肺炎链球菌（PRSP）和已经因青霉素结合蛋白（PBP）突变而对现有β-内酰胺类抗生素产生耐药性的非产β-内酰胺酶的氨苄青霉素耐药性流感嗜血杆菌具有抗菌作用。
• Carbapenem compounds
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：US07115595B2

  公开（公告）日：2006-10-03

  Carbapenem compounds having a substituted phenyl or a substituted thienyl directly attached to the 3-position of carbapenem nucleus as represented by the formula: wherein Ring E is benzene ring or thiophene ring; R1 is optionally OH-substituted C1-3 alkyl; R2 and R3 represent each H, optionally substituted lower alkyl, etc.; R is H, or a group which is hydrolyzed in the living body to regenerate a carboxyl group, etc.; X is O or S; and Y represents H, lower alkyl, etc., or pharmaceutically acceptable salts thereof and medicaments containing said compound as the active ingredient. These compounds exhibit an excellent antibacterial activity over a broad range of Gram-positive and Gram-negative bacteria, in particular, penicillin-resistant Streptococcus pneumoniae (PRSP) which has been isolated at an elevated frequency in recent years and thus causes a serious clinical problem, and Haemophilus influenzae which has acquired resistance against the existing β-lactam antibiotics over a wide scope due to penicillin-binding protein (PBP) mutations such as β-lactamase non-producing ampicillin-resistant (BLNAR) Haemophilus influenzae.

  具有取代苯基或取代噻吩基直接连接到碳青霉烷核的3位的碳青霉烷化合物，如下式所示： 其中，环E为苯环或噻吩环；R1为可选的OH取代的C1-3烷基；R2和R3分别表示H、可选取代的低级烷基等；R为H，或在生物体内水解生成羧基等的基团；X为O或S；Y表示H、低级烷基等，或其药学上可接受的盐，以及含有该化合物作为活性成分的药物。这些化合物在广泛的革兰氏阳性和革兰氏阴性细菌中表现出优异的抗菌活性，特别是对于最近年来频繁分离的耐青霉素的肺炎链球菌（PRSP）和已经因β-内酰胺酶非产生性的氨苄青霉素耐药（BLNAR）等原因而获得对现有β-内酰胺类抗生素的耐药性的流感嗜血杆菌具有重要的临床意义。