6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-4-one | 1129525-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-4-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(6-bromo-5-cyano-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-3-yl)oxolan-2-yl]methyl benzoate
• CAS: 1129525-95-6
• 化学式: C₃₃H₂₃BrN₄O₈
• 分子量: 683.472
• InChiKey: XPFYAMDGUYLFID-NYBSAPDNSA-N

物化性质

• 沸点：
  866.9±75.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-4-one 在 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到6-bromo-5-cyano-3-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-d]Pyrimidine Ribonucleosides

  摘要：

  The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2',3',5' tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.

  DOI：

  10.1080/15257770802089009
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 3.42h， 以50%的产率得到8-bromo-7-cyano-2,3,5-tri-O-benzoyl-7-deazainosine
  参考文献：
  名称：

  7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-d]Pyrimidine Ribonucleosides

  摘要：

  The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2',3',5' tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.

  DOI：

  10.1080/15257770802089009

文献信息

• 7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-<i>d</i>]Pyrimidine Ribonucleosides
  作者：Nunzia Ciliberti、Elisa Durini、Stefano Manfredini、Silvia Vertuani

  DOI：10.1080/15257770802089009

  日期：2008.4.18

  The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2',3',5' tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.