(1R)-1-tetrazolo[5,1-i]purin-7-yl-D-1,4-anhydro-ribitol | 37082-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-tetrazolo[5,1-i]purin-7-yl-D-1,4-anhydro-ribitol
• 英文别名: (1R)-1-Tetrazolo[5,1-i]purin-7-yl-D-1,4-anhydro-ribit；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(tetrazolo[5,1-f]purin-7-yl)oxolane-3,4-diol
• CAS: 37082-52-3
• 化学式: C₁₀H₁₁N₇O₄
• 分子量: 293.242
• InChiKey: IZINBYPJBKCTOK-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R)-1-tetrazolo[5,1-i]purin-7-yl-D-1,4-anhydro-ribitol 在 水 作用下， 反应 0.5h， 以80%的产率得到1-(β-D-ribofuranosyl)-4,6-dihydroimidazo[4,5-f][1,3,5]triazepin-5(1H)-one
  参考文献：
  名称：

  Photochemistry of 6-azidopurine ribonucleoside in aqueous solution

  摘要：

  In aqueous solution, 6-azido-9-beta-D-ribofuranosylpurine undergoes an efficient photoinduced purine ring expansion to give a novel imidazole-fused 1,3,5-triazepinone nucleoside and partial conversion into adenosine. The structure of the major product was established as 1-(beta-D-ribofuranosyl)-4,6-dihydroimidazo[4,5-f][1,3,5]triazepin-5(1H)-one based on HRMS and NMR spectral data. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.103
• 作为产物：
  描述：

  6-氯嘌呤核苷 生成 (1R)-1-tetrazolo[5,1-i]purin-7-yl-D-1,4-anhydro-ribitol
  参考文献：
  名称：

  Synthesis and Biological Evaluation of β-D-Pentofuranonucleoside Derivatives of 2-Azidoadenine and 6-Azidopurines

  摘要：

  beta-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines have been synthesized. The azido-tetrazolo tautomerism observed on such nucleoside analogues has been studied. The compounds were tested for their activity against HIV and HBV but they did not show significant antiviral effect.

  DOI：

  10.1081/ncn-120021964

文献信息

• Azide−Tetrazole Equilibrium of C-6 Azidopurine Nucleosides and Their Ligation Reactions with Alkynes
  作者：Mahesh K. Lakshman、Manish K. Singh、Damon Parrish、Raghavan Balachandran、Billy W. Day

  DOI：10.1021/jo902342z

  日期：2010.4.16

  nucleosides, access to the azido derivatives could be readily attained via displacement of BtO− from the O6-(benzotriazol-1-yl)inosine nucleosides by azide anion. Use of diphenylphosphoryl azide/DBU as a simple route to the acetyl-protected azido nucleosides was also evaluated, but this proved to be inferior. Since these azido nucleosides can exist in an azide·tetrazole equilibrium, the effect of solvent

  已经开发了C-6叠氮嘌呤核糖核苷和2'-脱氧核糖核苷的简便合成方法。对于甲硅烷基和乙酰基保护的以及未受保护的核苷，获得了叠氮基的衍生物，可以很容易地通过BTO的位移达到-从ø 6 -叠氮阴离子（苯并三唑-1-基）肌苷核苷。还评估了使用二苯基磷酰基叠氮化物/ DBU作为获得乙酰基保护的叠氮核苷的简单途径，但事实证明这是较差的。由于这些叠氮基核苷可以在叠氮化物·四唑平衡中存在，因此研究了溶剂极性对该平衡的影响。随后，对Cu介导的叠氮化物-炔（“点击”）连接进行了详细分析。双相CH 2 Cl 2 / H事实证明，2 O介质最适合连接反应，从而抑制了竞争中不希望的叠氮化物还原。有趣的是，尽管在CD 2 Cl 2和CD 2 Cl 2 / D 2中四唑基异构体占主导（约80％）。O，Cu催化的点击反应与甲硅烷基保护的核糖核苷和2'-脱氧核糖核苷顺利进行，从而导致C-6三唑基产物的收率非常好。因此，反应
• Synthesis and reactions of 6-methylsulfonyl-9-.beta.-D-ribofuranosylpurine
  作者：Ron Wetzel、Fritz Eckstein

  DOI：10.1021/jo00893a027

  日期：1975.3
• Synthesis of Potential Anticancer Agents. XIII. Ribosides of 6-Substituted Purines
  作者：James A. Johnson、H. Jeanette Thomas、Howard J. Schaeffer

  DOI：10.1021/ja01536a044

  日期：1958.2
• Synthesis and Biological Evaluation of β-D-Pentofuranonucleoside Derivatives of 2-Azidoadenine and 6-Azidopurines
  作者：Christophe Mathé、Thierry Lioux、Gilles Gosselin

  DOI：10.1081/ncn-120021964

  日期：2003.10

  beta-D-pentofuranonucleoside derivatives of 2-azidoadenine and 6-azidopurines have been synthesized. The azido-tetrazolo tautomerism observed on such nucleoside analogues has been studied. The compounds were tested for their activity against HIV and HBV but they did not show significant antiviral effect.
• Photochemistry of 6-azidopurine ribonucleoside in aqueous solution
  作者：Krzysztof Komodziński、Joanna Nowak、Jolanta Lepczyńska、Jan Milecki、Bohdan Skalski

  DOI：10.1016/j.tetlet.2012.02.103

  日期：2012.5

  In aqueous solution, 6-azido-9-beta-D-ribofuranosylpurine undergoes an efficient photoinduced purine ring expansion to give a novel imidazole-fused 1,3,5-triazepinone nucleoside and partial conversion into adenosine. The structure of the major product was established as 1-(beta-D-ribofuranosyl)-4,6-dihydroimidazo[4,5-f][1,3,5]triazepin-5(1H)-one based on HRMS and NMR spectral data. (C) 2012 Elsevier Ltd. All rights reserved.