O⁶-Benzyl-N²,3-etheno-2'-deoxyguanosine | 148437-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: O⁶-Benzyl-N²,3-etheno-2'-deoxyguanosine
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(4-phenylmethoxyimidazo[2,1-b]purin-1-yl)oxolan-3-ol
• CAS: 148437-95-0
• 化学式: C₁₉H₁₉N₅O₄
• 分子量: 381.391
• InChiKey: PVJAPKXTQKGHSP-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  O⁶-Benzyl-N²,3-etheno-2'-deoxyguanosine 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 N²,3-Etheno-2'-deoxyguanosine
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1021/jo00061a033
• 作为产物：
  描述：

  O6-苄基鸟苷 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium acetate 、 溶剂黄146 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 57.5h， 生成 O⁶-Benzyl-N²,3-etheno-2'-deoxyguanosine
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1021/jo00061a033

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).