(4R,5S)-4-methyl-5-phenyl-3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoyl]-1,3-oxazolidin-2-one | 1378433-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-4-methyl-5-phenyl-3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoyl]-1,3-oxazolidin-2-one
• CAS: 1378433-24-9
• 化学式: C₁₉H₂₆BNO₅
• 分子量: 359.23
• InChiKey: XSCDUMRLMWKEOZ-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-methyl-5-phenyl-3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoyl]-1,3-oxazolidin-2-one 在 锂硼氢 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 (R)-3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propan-1-ol
  参考文献：
  名称：

  Discovery of a Potent Boronic Acid Derived Inhibitor of the HCV RNA-Dependent RNA Polymerase

  摘要：

  A boronic acid moiety was found to be a critical pharmacophore for enhanced in vitro potency against wild-type hepatitis C replicons and known clinical polymorphic and resistant HCV mutant replicons. The synthesis, optimization, and structure-activity relationships associated with inhibition of HCV replication in a subgenomic replication system for a series of non-nucleoside boron-containing HCV RNA-dependent RNA polymerase (NS5B) inhibitors are described. A summary of the discovery of 3 (GSK5852), a molecule which entered clinical trials in subjects infected with HCV in 2011, is included.

  DOI：

  10.1021/jm400317w
• 作为产物：
  描述：

  (4R,5S)-3-acryloyl-4-methyl-5-phenyl-1,3-oxazolidin-2-one 、 联硼酸频那醇酯 在 双(2-二苯基磷苯基)醚 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 以47%的产率得到(4R,5S)-4-methyl-5-phenyl-3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Discovery of a Potent Boronic Acid Derived Inhibitor of the HCV RNA-Dependent RNA Polymerase

  摘要：

  A boronic acid moiety was found to be a critical pharmacophore for enhanced in vitro potency against wild-type hepatitis C replicons and known clinical polymorphic and resistant HCV mutant replicons. The synthesis, optimization, and structure-activity relationships associated with inhibition of HCV replication in a subgenomic replication system for a series of non-nucleoside boron-containing HCV RNA-dependent RNA polymerase (NS5B) inhibitors are described. A summary of the discovery of 3 (GSK5852), a molecule which entered clinical trials in subjects infected with HCV in 2011, is included.

  DOI：

  10.1021/jm400317w