<1-(15)N>-3',5'-Di-O-acetyl-2'-deoxyinosine | 161956-62-3

• 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: <1-(15)N>-3',5'-Di-O-acetyl-2'-deoxyinosine
• 英文别名: [1-15N]-3',5'-di-O-acetyl-2'-deoxyinosine；[(2R,3S,5R)-3-acetyloxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 161956-62-3
• 化学式: C₁₄H₁₆N₄O₆
• 分子量: 337.298
• InChiKey: FGIVQALFRSDINB-FKCSFACXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  <1-(15)N>-3',5'-Di-O-acetyl-2'-deoxyinosine 在 苄基三乙基氯化铵 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到<1-(15)N>-6-Chloro-9-(2'-deoxy-3',5'-di-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  [N,1-¹⁵N₂]-2‘-Deoxyadenosines

  摘要：

  An efficient route to deoxyadenosine derivatives labeled on both the amino group and nitrogen 1 is uncovered. First, 3',5'-di-O-acetyI-2'deoxy-1 -(2-nitrobenzenesuIfonyl)inosine (2a) and only 1.1 equiv of (NH4CI)-N-15 are used for labeling position 1 (1a*) through the isolation of the open intermediate and its cyclization with DBU in anhydrous CH3CN. Inosine 1a* is then converted to [N,1-N-15(2)]-3',5'-di-O-acetyl-N-6-benzoyl2'-deoxyadenosine (5a**, the precursor of 6a**) via a Pd/dppf-catalyzed chloride-to-benzamide replacement, by using again only 1.1 equiv of the labeling source.

  DOI：

  10.1021/ol050788w
• 作为产物：
  描述：

  [1-15N]-1-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)-5-(1-aminomethyleneamino)imidazole-4-[N-(2-nitrobenzenesulfonyl)]carboxamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到<1-(15)N>-3',5'-Di-O-acetyl-2'-deoxyinosine
  参考文献：
  名称：

  [N,1-¹⁵N₂]-2‘-Deoxyadenosines

  摘要：

  An efficient route to deoxyadenosine derivatives labeled on both the amino group and nitrogen 1 is uncovered. First, 3',5'-di-O-acetyI-2'deoxy-1 -(2-nitrobenzenesuIfonyl)inosine (2a) and only 1.1 equiv of (NH4CI)-N-15 are used for labeling position 1 (1a*) through the isolation of the open intermediate and its cyclization with DBU in anhydrous CH3CN. Inosine 1a* is then converted to [N,1-N-15(2)]-3',5'-di-O-acetyl-N-6-benzoyl2'-deoxyadenosine (5a**, the precursor of 6a**) via a Pd/dppf-catalyzed chloride-to-benzamide replacement, by using again only 1.1 equiv of the labeling source.

  DOI：

  10.1021/ol050788w

文献信息

• Synthesis of [1-15N]-Labeled 2'-Deoxyinosine and 2'-Deoxyadenosine
  作者：Lorenzo De Napoli、Anna Messere、Daniela Montesarchio、Gennaro Piccialli

  DOI：10.1021/jo00112a053

  日期：1995.4