(4R,5S)-3-((S)-3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propanoyl)-4-methyl-5-phenyloxazolidin-2-one | 1440415-08-6

• 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: (4R,5S)-3-((S)-3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propanoyl)-4-methyl-5-phenyloxazolidin-2-one
• CAS: 1440415-08-6
• 化学式: C₂₇H₃₄BNO₆
• 分子量: 479.381
• InChiKey: GWWSSWSPVRBWLJ-WTIAFYNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-((S)-3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propanoyl)-4-methyl-5-phenyloxazolidin-2-one 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以1.03 g的产率得到(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：

  联硼酸频那醇酯 在 四氯化钛 、 双(2-二苯基磷苯基)醚 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.92h， 生成 (4R,5S)-3-((S)-3-(benzyloxy)-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)propanoyl)-4-methyl-5-phenyloxazolidin-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