(2S,3R,2'S,3'R)-[2,2]bioxiranyl-3,3-dicarboxylic acid | 372969-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3R,2'S,3'R)-[2,2]bioxiranyl-3,3-dicarboxylic acid
• 英文别名: (2S,3R)-3-[(2R,3S)-3-carboxyoxiran-2-yl]oxirane-2-carboxylic acid
• CAS: 372969-61-4
• 化学式: C₆H₆O₆
• 分子量: 174.11
• InChiKey: IRDWPCCLUCUYGV-MMPJQOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,2'S,3'R)-[2,2]bioxiranyl-3,3-dicarboxylic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.84h， 生成 (2R,3R,4R,5R)-2,5-Bis-(2-fluoro-benzylsulfanyl)-3,4-dihydroxy-hexanedioic acid bis-[((1S,2R)-2-hydroxy-indan-1-yl)-amide]
  参考文献：
  名称：

  Synthesis of Potent C₂-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents

  摘要：

  The synthesis of novel, potent diol-based HIV-1 protease inhibitors, having either -SAr, -SCH2-Ar, or -SCH2R groups as P1/P1' substituents is described. They can be prepared using a straightforward synthesis involving a thiol nucleophilic ring opening of a diepoxide. Inhibitor 13 was found to be a potent inhibitor of HIV-1 PR, showing good antiviral activity in a cell-based assay.

  DOI：

  10.1021/jm0011169
• 作为产物：
  描述：

  (2S,3R,2'S,3'R)-3'-hydroxymethyl-([2,2]bioxiranyl-3-yl)methanol 在 ruthenium trichloride 、 高碘酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.25h， 以86%的产率得到(2S,3R,2'S,3'R)-[2,2]bioxiranyl-3,3-dicarboxylic acid
  参考文献：
  名称：

  Synthesis of Potent C₂-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents

  摘要：

  The synthesis of novel, potent diol-based HIV-1 protease inhibitors, having either -SAr, -SCH2-Ar, or -SCH2R groups as P1/P1' substituents is described. They can be prepared using a straightforward synthesis involving a thiol nucleophilic ring opening of a diepoxide. Inhibitor 13 was found to be a potent inhibitor of HIV-1 PR, showing good antiviral activity in a cell-based assay.

  DOI：

  10.1021/jm0011169

文献信息

• Synthesis of Potent <i>C</i>₂-Symmetric, Diol-Based HIV-1 Protease Inhibitors. Investigation of Thioalkyl and Thioaryl P1/P1‘ Substituents
  作者：Anna Mühlman、Björn Classon、Anders Hallberg、Bertil Samuelsson

  DOI：10.1021/jm0011169

  日期：2001.10.1

  The synthesis of novel, potent diol-based HIV-1 protease inhibitors, having either -SAr, -SCH2-Ar, or -SCH2R groups as P1/P1' substituents is described. They can be prepared using a straightforward synthesis involving a thiol nucleophilic ring opening of a diepoxide. Inhibitor 13 was found to be a potent inhibitor of HIV-1 PR, showing good antiviral activity in a cell-based assay.