(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(7-nitro-8-phenyl-3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3,4-diyl diacetate | 1547236-47-4

• 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: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(7-nitro-8-phenyl-3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 1547236-47-4
• 化学式: C₂₄H₂₂N₆O₉
• 分子量: 538.473
• InChiKey: XNOOXLUNWCRCRY-UFRIGAJXSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  179.28
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(7-nitro-8-phenyl-3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3,4-diyl diacetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(7-amino-8-phenyl-3H-imidazo[2,1-i]purin-3-yl)-tetrahydrofuran-3,4-diyl Diacetate
  参考文献：
  名称：

  A Copper-Catalyzed Domino Route toward Purine-Fused Tricyclic Derivatives

  摘要：

  Purine-fused tricyclic derivatives have been synthesized via a copper-catalyzed domino Michael/oxidative cross-coupling reaction between adenines and nitroolefins for the first time. With air as the oxidant, this method has high regioselectivity, which provides a new route for constructing purine-nucleoside-conjugated systems with two newly formed C-N bonds. Meanwhile, purine nucleosides with an exocyclic amino group could be obtained easily by simple reduction, which may lead to potential applications in fluorescence recognition of various bases in vivo.

  DOI：

  10.1021/jo4025489
• 作为产物：
  描述：

  反式硝基苯乙烯 、 2',3',5'-三乙酰腺苷 在 copper(I) bromide 、 三甲基乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以65%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(7-nitro-8-phenyl-3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3,4-diyl diacetate
  参考文献：
  名称：

  A Copper-Catalyzed Domino Route toward Purine-Fused Tricyclic Derivatives

  摘要：

  Purine-fused tricyclic derivatives have been synthesized via a copper-catalyzed domino Michael/oxidative cross-coupling reaction between adenines and nitroolefins for the first time. With air as the oxidant, this method has high regioselectivity, which provides a new route for constructing purine-nucleoside-conjugated systems with two newly formed C-N bonds. Meanwhile, purine nucleosides with an exocyclic amino group could be obtained easily by simple reduction, which may lead to potential applications in fluorescence recognition of various bases in vivo.

  DOI：

  10.1021/jo4025489