4-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-2-phenylpyrimidine | 652972-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-2-phenylpyrimidine
• 英文别名: 4-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylpyrimidine
• CAS: 652972-38-8
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: NTBOUHLENOSQFD-BRWVUGGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-2-phenylpyrimidine 在 三氟乙酸 、 DOWEX resin basic form 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.5h， 以54%的产率得到2-phenyl-4-(D-arabino-tetritol-1-yl)pyrimidine
  参考文献：
  名称：

  Synthesis of Acyclic C‐Nucleoside Analogues Using (E)‐1,2‐Dideoxy‐1‐dimethylamino‐4,5:6,7‐di‐O‐isopropylidene‐d‐arabino‐hept‐1‐en‐3‐ulose

  摘要：

  1-Deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hex-2-ulose reacted with N,N-dimethylformamide dimethyl acetal and tert-butoxy [bis(dimethylamino)] methane, respectively, to furnish (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose. This push-pull activated heptenulose underwent ring closure reactions with various N,N'-nucleophiles like hydrazine hydrate, amidinium, guanidinium and isothiouronium salts in the presence of bases to yield pyrazole and pyrimidine derivatives, respectively, all of which derivatized with a di-O-isopropylidenated tetritol side chain. The isopropylidene groups were removed with methanolic HCl in the pyrazole series, whereas aq TFA was used in the case of pyrimidine analogues.

  DOI：

  10.1081/car-120026457
• 作为产物：
  描述：

  1-deoxy-3,4:5,6-di-O-isopropylidene-D-fructose 在 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 4-(1,2:3,4-di-O-isopropylidene-D-arabino-tetritol-1-yl)-2-phenylpyrimidine
  参考文献：
  名称：

  Synthesis of Acyclic C‐Nucleoside Analogues Using (E)‐1,2‐Dideoxy‐1‐dimethylamino‐4,5:6,7‐di‐O‐isopropylidene‐d‐arabino‐hept‐1‐en‐3‐ulose

  摘要：

  1-Deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hex-2-ulose reacted with N,N-dimethylformamide dimethyl acetal and tert-butoxy [bis(dimethylamino)] methane, respectively, to furnish (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose. This push-pull activated heptenulose underwent ring closure reactions with various N,N'-nucleophiles like hydrazine hydrate, amidinium, guanidinium and isothiouronium salts in the presence of bases to yield pyrazole and pyrimidine derivatives, respectively, all of which derivatized with a di-O-isopropylidenated tetritol side chain. The isopropylidene groups were removed with methanolic HCl in the pyrazole series, whereas aq TFA was used in the case of pyrimidine analogues.

  DOI：

  10.1081/car-120026457