2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine | 149725-73-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(phenylsulfanylmethyl)oxolan-3-yl] acetate
• CAS: 149725-73-5
• 化学式: C₂₀H₂₁N₅O₅S
• 分子量: 443.483
• InChiKey: KCRIGRJWVCSTSN-WVSUBDOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 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：
  157
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine 在 二乙胺基三氟化硫 、 三氯化锑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2',3'-Di-O-acetyl-5'-fluoro-5'-S-phenyl-5'-thioadenosine
  参考文献：
  名称：

  Fluorination at C5′ of nucleosides. Synthesis of the new class of 5′-fluoro-5′-S-aryl (alkyl) thionucleosides from adenosine.

  摘要：

  DOI：

  10.1016/s0040-4039(00)82174-7
• 作为产物：
  描述：

  乙酸酐 、 5'-S-phenyl-5'-thioadenosine 在 吡啶 作用下， 反应 7.0h， 以98%的产率得到2',3'-Di-O-acetyl-5'-S-phenyl-5'-thioadenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 80. Synthesis of 5'-S-(Alkyl and aryl)-5'-fluoro-5'-thioadenosines with Xenon Difluoride or (Diethylamido)sulfur Trifluoride, Hydrolysis in Aqueous Buffer, and Inhibition of S-Adenosyl-L-homocysteine hydrolase by derived "Adenosine 5'-Aldehyde" Species

  摘要：

  Treatment of 5/-S-(alkyl and aryl)-5'-thioadenosine derivatives 2 with XeF2, or the corresponding sulfoxides 3 with DAST/SbCl3, gave diastereomeric 5'-fluoro compounds which were deprotected to give the 5'-S-(alkyl and aryl)-5'-fluoro-5'-thioadenosine analogues 5. Stereochemistry was established by X-ray crystallography, and F-19 NMR chemical shifts were definitive for configurationally-related 5'-fluoro diastereomers. Sulfoxidation and thermolysis afforded the fluoromethylene analogues with retained relative configuration. The nucleoside 5'-alpha-fluoro thioethers 5 underwent spontaneous hydrolysis in aqueous buffer to give derived ''adenosine 5'-aldehyde'' species which caused potent time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jo00082a010

文献信息

• Nucleic acid related compounds. 79. Efficient conversions of thioethers to .alpha.-fluoro thioethers with DAST or DAST/antimony(III) chloride
  作者：Morris J. Robins、Stanislaw F. Wnuk

  DOI：10.1021/jo00067a009

  日期：1993.7

  Dialkyl or alkyl aryl thioethers, including nucleoside thioethers, undergo virtually quantitative conversion to alpha-fluoro thioethers with (diethylamino)sulfur trifluoride (DAST) in dichloromethane at ambient temperature. Antimony(III) chloride catalyzes the process.
• Nucleic Acid Related Compounds. 82. Conversions of Adenosine to Inosine 5′-Thioether Derivatives with<i>Aspergillus oryzae</i>Adenosine Deaminase or Alkyl Nitrites. Substrate and Inhibitory Activities of Inosine 5′-Thioether Derivatives with Purine Nucleoside Phosphorylase
  作者：Stanislaw F. Wnuk、Johanna D. Stoeckler、Morris J. Robins

  DOI：10.1080/15257779408013249

  日期：1994.3

  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.