N²,3-Ethenoguanosine | 108060-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N²,3-Ethenoguanosine
• 英文别名: n2,3-Ethenoguanosine；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5H-imidazo[2,1-b]purin-4-one
• CAS: 108060-85-1
• 化学式: C₁₂H₁₃N₅O₅
• 分子量: 307.266
• InChiKey: CLYBQLKNRHAHBL-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  鸟苷 在 palladium on activated charcoal sodium acetate buffer 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 N²,3-Ethenoguanosine
  参考文献：
  名称：

  Synthesis and properties of N2,3-ethenoguanosine and N2,3-ethenoguanosine 5'-diphosphate

  摘要：

  DOI：

  10.1021/jo00388a007

文献信息

• N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization
  作者：Rajesh Khazanchi、Pei Lin Yu、Francis Johnson

  DOI：10.1021/jo00061a033

  日期：1993.4

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).
• Synthesis and properties of N2,3-ethenoguanosine and N2,3-ethenoguanosine 5'-diphosphate
  作者：Jaroslaw T. Kusmierek、David E. Jensen、Sylvia J. Spengler、Ryszard Stolarski、B. Singer

  DOI：10.1021/jo00388a007

  日期：1987.6