(2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid | 588729-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid
• CAS: 588729-32-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: WQGBZYWITKOMCR-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid 在 吗啉 、 lithium hydroxide 、 四(三苯基膦)钯 、 N-羟基-7-氮杂苯并三氮唑 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4R)-3-[(2S,4R)-4-benzyl-2-[tert-butyl(dimethyl)silyl]oxy-5-[[(3S,4S)-3-hydroxy-3,4-dihydro-2H-chromen-4-yl]amino]-5-oxopentanoyl]-N-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide
  参考文献：
  名称：

  Design and synthesis of highly potent HIV protease inhibitors with activity against resistant virus

  摘要：

  A series of highly potent HIV protease inhibitors have been designed and synthesized. These compounds are active against various clinical viral isolates as well as wild-type virus. The synthesis and biological activity of these HIV protease inhibitors are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00262-2
• 作为产物：
  描述：

  3R,5S-3-Benzyl-5-hydroxymethyl-4,5-dihydro-2(3H)-furanon 在 jones' reagent 作用下， 以 丙酮 为溶剂， 生成 (2S,4R)-4-Benzyl-5-oxo-tetrahydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of highly potent HIV protease inhibitors with activity against resistant virus

  摘要：

  A series of highly potent HIV protease inhibitors have been designed and synthesized. These compounds are active against various clinical viral isolates as well as wild-type virus. The synthesis and biological activity of these HIV protease inhibitors are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00262-2

文献信息

• Synthesis of novel HIV protease inhibitors (PI) with activity against PI-resistant virus
  作者：Subharekha Raghavan、Zhijian Lu、Teresa Beeson、Kevin T. Chapman、William A. Schleif、David B. Olsen、Mark Stahlhut、Carrie A. Rutkowski、Lori Gabryelski、Emilio Emini、James R. Tata

  DOI：10.1016/j.bmcl.2007.07.040

  日期：2007.10

  A series of HIV protease inhibitors with modifications on the P3 position have been designed and synthesized. These compounds exhibit excellent antiviral activity against both the wild type enzyme and PI-resistant clinical viral isolates. The synthesis and biological activity of the compounds are described. (C) 2007 Elsevier Ltd. All rights reserved.