9-{(2R,3S,4R,5R)-3-Hydroxy-4-iodo-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one | 183728-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-{(2R,3S,4R,5R)-3-Hydroxy-4-iodo-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one
• CAS: 183728-88-3
• 化学式: C₃₀H₂₇IN₄O₅
• 分子量: 650.473
• InChiKey: CXJUVWUVWPIIDY-KDJXNGHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  111.49
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  9-{(2R,3S,4R,5R)-3-Hydroxy-4-iodo-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903
• 作为产物：
  描述：

  2',3'-anhydroinosine 在 吡啶 、 三氟化硼乙醚 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 9-{(2R,3S,4R,5R)-3-Hydroxy-4-iodo-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903