1-Benzyl-2',3'-isopropyliden-inosin | 7026-47-3

• 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-Benzyl-2',3'-isopropyliden-inosin
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-benzylpurin-6-one
• CAS: 7026-47-3
• 化学式: C₂₀H₂₂N₄O₅
• 分子量: 398.418
• InChiKey: JQGMSUSVTNWYAN-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  98.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-Benzyl-2',3'-isopropyliden-inosin 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到1-Benzyl-9-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1,2,3,9-tetrahydro-purin-6-one
  参考文献：
  名称：

  Regioselective BH3–hydride reduction of inosine derivatives

  摘要：

  Reaction of inosine derivatives with BH3-THF resulted in the regioselective reduction of the purine nucleus to afford 2,3-dihydroinosine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02209-2
• 作为产物：
  描述：

  溴甲苯 、 肌苷 在 碳酸氢钠 作用下， 生成 1-Benzyl-2',3'-isopropyliden-inosin
  参考文献：
  名称：

  An efficient synthesis of futalosine

  摘要：

  Futalosine is a naturally occurring nucleoside comprised of an inosine core with a 3-carboxyphenyl methylene ketone functionality replacing the C-5' hydroxyl. Recent studies have shown that it is a key intermediate in an alternative biosynthetic pathway that generates menaquinone in a variety of bacterial species. Here we report the first synthesis of futalosine in seven steps from inosine in an overall 17% yield. This work will enable further studies on menaquinone biosynthesis in pathogenic bacteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.010

文献信息

• Intramolecular Cation−π Interactions As the Driving Force To Restrict the Conformation of Certain Nucleosides
  作者：Elena Casanova、Eva-María Priego、María-Luisa Jimeno、Leire Aguado、Ana Negri、Federico Gago、María-José Camarasa、María-Jesús Pérez-Pérez

  DOI：10.1021/jo902677s

  日期：2010.3.19

  Despite the well-established importance of intermolecular cation-pi interactions in molecular recognition, intramolecular cation-pi interactions have been less studied. Here we describe how the simultaneous presence of an aromatic ring at the 5'-position of an inosine derivative and a positively charged imidazolium ring in the purine base drive the conformation of the nucleoside toward a very major conformer in solution that is stabilized by an intramolecular cation-pi interaction. Therefore, the cation-pi interaction between imidazolium ions and aromatic rings can also be proposed in the design of small molecules where this type of interaction is desirable. The imidazolium ion can be obtained by a simple acidification of the pH of the media. So a simple change in pH can shift the conformational equilibrium from a random to a restricted conformation stabilized by an intramolecular cation-pi interaction. Thus the here described nucleosides can be considered as a new class of pH-dependent conformationally switchable molecules.