4-Amino-8-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8H-pteridin-7-one | 195442-57-0

• 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: 4-Amino-8-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8H-pteridin-7-one
• 英文别名: 4-amino-8-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]pteridin-7-one
• CAS: 195442-57-0
• 化学式: C₃₂H₃₁N₅O₆
• 分子量: 581.628
• InChiKey: JHFFGWBFPAEWAI-ZRRKCSAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 4-Amino-8-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8H-pteridin-7-one 以75%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(4-amino-7-oxo-7H-pteridin-8-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188
• 作为产物：
  描述：

  4-N,N-dimethylaminomethyleneimino-7(8H)-pteridone 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 4-Amino-8-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-8H-pteridin-7-one
  参考文献：
  名称：

  Pteridine Nucleosides—New Versatile Building Blocks in Oligonucleotide Synthesis

  摘要：

  Chemical syntheses of 1-(2-deoxy-beta-D-ribofuranosyl)lumazines and isopterins as well as 8-(2-deoxy-beta-D-ribofuranosyl)-4-amino-7(8H)pteridones and -isoxanthopterins have been developed to make the structural analogs of the naturally occurring 2'-deoxyribonucleosides in the pteridine series available. The corresponding phosphoramidites have been used in machine-aided solid-support syntheses leading to new types of fluorescence labeled oligonucleotides. The effects of the various fluorophors on duplex formation and as labels for enzyme reactions is demonstrated.

  DOI：

  10.1080/07328319708006188

文献信息

• Pteridine Nucleosides Analogs of 2′-Deoxyadenosine as Building Blocks for Oligonucleotide Synthesis
  作者：Oliver Jungmann、Wolfgang Pfleiderer

  DOI：10.1080/07328319708002964

  日期：1997.5

  The synthesis, configuration and conformation of adenosine analogous pteridine nucleosides and their conversion into the monomeric building blocks for the automated application in an DNA synthesizer is described.