(R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate | 104392-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate
• 英文别名: R-(2-oxo-N-phenyloxazolidin-5-yl)methyl tosylate；(R)-[5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl]-methyl 4-methylbenzenesulfonate；[(5R)-2-oxo-3-phenyl-1,3-oxazolidin-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 104392-60-1
• 化学式: C₁₇H₁₇NO₅S
• 分子量: 347.392
• InChiKey: HYWWZBVPIWRDAW-OAHLLOKOSA-N

物化性质

• 沸点：
  505.6±19.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate 在 sodium azide 、 18-冠醚-6 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以88%的产率得到(R)-(3-phenyl-2-oxo-5-oxazolidinyl)methyl azide
  参考文献：
  名称：

  Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group

  摘要：

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.

  DOI：

  10.1021/jm00128a003
• 作为产物：
  描述：

  (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 PS(polymer)-TsCl 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.25h， 生成 (R)-<5-(hydroxymethyl)-3-phenyl-2-oxooxazolidinyl>-methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Polymer-Aided Stereodivergent Synthesis (PASS):  A New Concept for the Discrete Preparation of Optical Antipodes

  摘要：

  [GRAPHICS]A new concept for the discrete preparation of optical antipodes is reported. The approach makes use of a cyclization/cleavage procedure that has been applied to polymer-supported quasi-meso compound 1, containing a polymeric leaving group and a regular leaving group. Two-directional cyclization leads to the formation and separation of quasi-enantiomers 2 and 3 simultaneously, with one being immobilized and one free in solution. Treatment of 2 and 3 with appropriate nucleophiles gives discrete enantiomers 4 and 5.

  DOI：

  10.1021/ol015723h

文献信息

• Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04705799A1

  公开（公告）日：1987-11-10

  Novel aminomethyl oxooxazolidinyl benzene derivatives, including the sulfides, sulfoxides, sulfones and sulfonamides, such as (l)-N-[3-[4-(methylsulfinyl)phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide, possess useful antibacterial activity.

  新型氨甲基氧噁唑啉基苯衍生物，包括硫醚、亚硫醚、磺酰和磺酰胺衍生物，如（l）-N-[3-[4-(甲基亚磺基)苯基]-2-氧噁唑啉-5-基甲基]乙酰胺，具有有用的抗菌活性。
• Glycidyl Tosylate is a Viable Starting Material for Oxazolidinone Antibacterials
  作者：Cho-Rom Kim、Soo-Y. Ko

  DOI：10.5012/bkcs.2011.32.12.4450

  日期：2011.12.20
• Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 1. The B group
  作者：Walter A. Gregory、David R. Brittelli、C. L. J. Wang、Mark A. Wuonola、Ronald J. McRipley、David C. Eustice、Virginia S. Eberly、Andrew M. Slee、Martin Forbes、P. T. Bartholomew

  DOI：10.1021/jm00128a003

  日期：1989.8

  The synthesis and structure/activity studies of the effect of varying the "B" group in a series of oxazolidinone antibacterials (I) are described. Two synthetic routes were used: (1) alkylation of aniline with glycidol followed by dialkyl carbonate heterocyclization to afford I (A = H, B = OH), whose arene ring was further elaborated by using electrophilic aromatic substitution methodology; (2) cycloaddition of substituted aryl isocyanates with epoxides to give A and B with a variety of values. I with B = OH or Br were converted to other "B" functionalities by using SN2 methodology. Antibacterial evaluation of compounds I with A = acetyl, isopropyl, methylthio, methylsulfinyl, methylsulfonyl, and sulfonamido and a variety of different "B" groups against Staphylococcus aureus and Enterococcus faecalis concluded that the compounds with B = aminoacyl, and particularly acetamido, were the most active of those examined in each A series, possessing MICs in the range of 0.5-4 micrograms/mL for the most active compounds described.
• Polymer-Aided Stereodivergent Synthesis (PASS):  A New Concept for the Discrete Preparation of Optical Antipodes
  作者：Peter ten Holte、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1021/ol015723h

  日期：2001.4.1

  [GRAPHICS]A new concept for the discrete preparation of optical antipodes is reported. The approach makes use of a cyclization/cleavage procedure that has been applied to polymer-supported quasi-meso compound 1, containing a polymeric leaving group and a regular leaving group. Two-directional cyclization leads to the formation and separation of quasi-enantiomers 2 and 3 simultaneously, with one being immobilized and one free in solution. Treatment of 2 and 3 with appropriate nucleophiles gives discrete enantiomers 4 and 5.