N-benzoyldeoxyguanosine | 61773-87-3

• 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: N-benzoyldeoxyguanosine
• 英文别名: N-Benzoyl-2'-deoxyguanosine；N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]benzamide
• CAS: 61773-87-3
• 化学式: C₁₇H₁₇N₅O₅
• 分子量: 371.352
• InChiKey: YUMFYDCQASKKJX-QJPTWQEYSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-benzoyldeoxyguanosine 在 乙二胺 作用下， 反应 20.0h， 以50%的产率得到2'-脱氧鸟苷
  参考文献：
  名称：

  Debenzoylation of N-benzoylnucleoside derivatives with ethylenediamine-phenol

  摘要：

  DOI：

  10.1016/s0040-4039(01)82847-1
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 ammonium hydroxide 作用下， 反应 7.75h， 生成 N-benzoyldeoxyguanosine
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200

文献信息

• BORANE-AMINE COMPLEXES - VERSATILE REAGENTS IN THE CHEMISTRY OF NUCLEIC ACIDS AND THEIR ANALOGS
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Barbara Ramsay Shaw

  DOI：10.1081/ncn-100002464

  日期：2001.3.31

  A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4'-dimethoxytrityl (DMT) cation. Neutralization of the cation eliminated the boranophosphate group degradation during acidic DMT deprotection and allowed milder acidic conditions for the deprotection.
• An Improved Transient Method for the Synthesis of<i>N</i>-Benzoylated Nucleosides
  作者：Xue-Feng Zhu、Howard J. Williams、A. Ian Scott

  DOI：10.1081/scc-120017200

  日期：2003.1.5

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
• Debenzoylation of N-benzoylnucleoside derivatives with ethylenediamine-phenol
  作者：Richard W. Barnett、Robert L. Letsinger

  DOI：10.1016/s0040-4039(01)82847-1

  日期：1981.1