O^2;_,O3'_,O5'-tris-trimethylsilyl-N⁶,N⁶-dibenzoyladenosine | 610305-23-2

• 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: O^2;_,O3'_,O5'-tris-trimethylsilyl-N⁶,N⁶-dibenzoyladenosine
• 英文别名: N-benzoyl-N-[9-[(2R,3R,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 610305-23-2
• 化学式: C₃₃H₄₅N₅O₆Si₃
• 分子量: 692.007
• InChiKey: WBZKMOCILQJLQL-IXXGIDSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O^2;_,O3'_,O5'-tris-trimethylsilyl-N⁶,N⁶-dibenzoyladenosine 在 吡啶 、 ammonium hydroxide 作用下， 反应 0.33h， 以97%的产率得到N6-苯甲酰基腺苷
  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
• 作为产物：
  描述：

  腺苷 在 吡啶 作用下， 反应 7.5h， 生成 O^2;_,O3'_,O5'-tris-trimethylsilyl-N⁶,N⁶-dibenzoyladenosine
  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

• 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.