Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester | 156430-65-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-2-(benzenesulfonylmethyl)-5-(6-oxo-1H-purin-9-yl)oxolan-3-yl] acetate
• CAS: 156430-65-8
• 化学式: C₂₀H₂₀N₄O₈S
• 分子量: 476.467
• InChiKey: ZBCWIWQLWOTHBA-WVSUBDOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到5'-deoxy-5'-(phenylsulfonyl)inosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 82. Conversions of Adenosine to Inosine 5′-Thioether Derivatives withAspergillus oryzaeAdenosine Deaminase or Alkyl Nitrites. Substrate and Inhibitory Activities of Inosine 5′-Thioether Derivatives with Purine Nucleoside Phosphorylase

  摘要：

  Adenosine derivatives lacking a 5'-hydroxyl group seldom act as alternative substrates of adenosine deaminases from calf intestine and other mammalian sources. A deaminase from Aspergillus oryzae deaminated adenosine 5'-thioether derivatives cleanly and more efficiently than alkyl nitrites. The inosine derivatives were very poor alternative substrates and weak inhibitors of purine nucleoside phosphorylase.

  DOI：

  10.1080/15257779408013249
• 作为产物：
  描述：

  2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine 在 亚硝酸特丁酯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-benzenesulfonylmethyl-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 82. Conversions of Adenosine to Inosine 5′-Thioether Derivatives withAspergillus oryzaeAdenosine Deaminase or Alkyl Nitrites. Substrate and Inhibitory Activities of Inosine 5′-Thioether Derivatives with Purine Nucleoside Phosphorylase

  摘要：

  Adenosine derivatives lacking a 5'-hydroxyl group seldom act as alternative substrates of adenosine deaminases from calf intestine and other mammalian sources. A deaminase from Aspergillus oryzae deaminated adenosine 5'-thioether derivatives cleanly and more efficiently than alkyl nitrites. The inosine derivatives were very poor alternative substrates and weak inhibitors of purine nucleoside phosphorylase.

  DOI：

  10.1080/15257779408013249