[(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride | 198021-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride
• 英文别名: 3-Oxazolidineacetyl chloride, 2-oxo-4,5-diphenyl-, (4S,5R)-；2-[(4S,5R)-2-oxo-4,5-diphenyl-1,3-oxazolidin-3-yl]acetyl chloride
• CAS: 198021-41-9
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: ONCPUTDNWCACRL-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines

  摘要：

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.

  DOI：

  10.1002/chem.19970030909
• 作为产物：
  描述：

  ethyl [(4S,5R)-4,5-diphenyloxazolidin-2-on-3-yl]acetate 在 草酰氯 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.5h， 生成 [(4S,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl]acetyl chloride
  参考文献：
  名称：

  A practical synthesis of enantiopure 4,4,4-trifluoro-allo-threonine from an easily available fluorinated building block

  摘要：

  A practical method to prepare enantiopure 4,4,4-trifluoro-allo-threonine was developed by using an easily available fluorinated building block and a chiral auxiliary as starting materials. Trifluoroacetic anhydride was annulated with a ketene, derived from a glycine equivalent bearing a chiral oxazolidinone [(4S,5R)-4,5-diphenyloxazolidin-2-one], and acetone to afford a trifluoromethylated alpha,beta-unsaturated lactone. The asymmetric hydride reduction of the alpha,beta-unsaturated lactone proceeded with excellent stereoselectivity to give the corresponding (2R,3S)-4-oxapentan-5-olide derivative exclusively (diastereopurity, 99%). From the reduced product thus obtained, protecting groups were readily removed by acid treatment and subsequent catalytic hydrogenolysis to afford enantiopure (2R,35)-4,4,4-trifluoro-allo-threonine in an excellent yield (7 steps, 51% overall yield). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.041

文献信息

• [EN] CARBACEPHEM BETA-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES BÊTA-LACTAMES CARBACÉPHÈMES
  申请人：ACHAOGEN INC

  公开号：WO2010123997A1

  公开（公告）日：2010-10-28

  Carbacephem β-lactam antibiotics having chemical structures (I) and (II) are disclosed: including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R6 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

  Carbacephem β-内酰胺类抗生素具有化学结构（I）和（II）如下：包括立体异构体、药用可接受的盐、酯和前药，其中Ar2、R1、R2和R6如本文所定义。这些化合物对治疗细菌感染特别有效，尤其是由耐甲氧西林金黄色葡萄球菌引起的感染。
• [EN] CARBACEPHEM ß-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES BÊTA-LACTAMES À CARBACÉPHÈME
  申请人：ACHAOGEN INC

  公开号：WO2009055696A1

  公开（公告）日：2009-04-30

  Carbacephem β-lactam antibiotics having the following chemical structures (I) and (II) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R3 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

  Carbacephem β-内酰胺抗生素具有以下化学结构（I）和（II），包括立体异构体、药用可接受的盐、酯和前药，其中Ar2、R1、R2和R3如本文所定义。这些化合物可用于治疗细菌感染，特别是由耐甲氧西林葡萄球菌属引起的感染。
• 2-oxa-isocephem compounds, compositions containing same and processes of
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04831026A1

  公开（公告）日：1989-05-16

  A 2-oxa-isocephem compound of the formula (1): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined, pharmaceutically acceptable salts thereof, esters of the carboxy group in the 4-position thereof and quaternary ammonium salts thereof, composition containing the same and processes for preparing the same are disclosed. The compound is useful as an antimicrobial compound.

  本发明公开了一种式子为(1)的2-氧杂异头孢烷化合物：##STR1## 其中R.sup.1，R.sup.2和R.sup.3如定义所示，其药学上可接受的盐，其4-位置上羧基的酯和季铵盐，以及含有该化合物的组合物和制备该化合物的方法。该化合物可用作抗微生物化合物。
• [EN] CARBACEPHEM ß-LACTAM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES DE TYPE ?-LACTAME À BASE DE CARBACÉPHÈME
  申请人：ACHAOGEN INC

  公开号：WO2010030811A3

  公开（公告）日：2010-08-12
• Practical Access to Carbacephem Intermediates via Asymmetric [2 + 2] Ketene−Imine Cycloaddition
  作者：Claudio Palomo、Iñaki Ganboa、Agata Kot、Leszek Dembkowski

  DOI：10.1021/jo980515x

  日期：1998.9.1