(E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose | 652972-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose
• 英文别名: (E)-3-(dimethylamino)-1-[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-one
• CAS: 652972-31-1
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: WWMIARQQQVKWTO-MABIMBCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose 在 sodium ethanolate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 21.5h， 生成 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：

  Bredereck 试剂 、 1-deoxy-3,4:5,6-di-O-isopropylidene-D-fructose 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到(E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-D-arabino-hept-1-en-3-ulose
  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

文献信息

• Synthesis of Acyclic <i>C</i>‐Nucleoside Analogues Using (<i>E</i>)‐1,2‐Dideoxy‐1‐dimethylamino‐4,5:6,7‐di‐<i>O</i>‐isopropylidene‐<scp>d</scp>‐<i>arabino</i>‐hept‐1‐en‐3‐ulose
  作者：Karen Methling、Jürgen Kopf、Manfred Michalik、Helmut Reinke、Christiane Bürger、Heiderose Oberender、Klaus Peseke

  DOI：10.1081/car-120026457

  日期：2003.12.31

  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.