2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)-N²-methylguanosine | 130469-18-0

• 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: 2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)-N²-methylguanosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-[1,3-benzodithiol-2-yl(methyl)amino]-6-oxo-3H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 130469-18-0
• 化学式: C₂₄H₂₅N₅O₈S₂
• 分子量: 575.623
• InChiKey: LNLUHEMTNQFQBZ-RCAWKPMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  154.94
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)-N²-methylguanosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以94%的产率得到2’,3’,5’-三-O-乙酰基-2N,2N-二甲基鸟苷
  参考文献：
  名称：

  A convenient method for the synthesis of N2,N2-dimethylguanosine by reductive carbon-sulfur bond cleavage with tributyltin hydride

  摘要：

  A new method for the N-methylation of guanosine is described. The 1,3-benzodithiol-2-yl group was introduced into the 2-amino group of 2',3',5'-tri-O-acetylguanosine (3) and then converted into a methyl group by reductive C-S bond cleavage with tributyltin hydride. This method was also applied to the synthesis of N2,N2-dimethylguanosine. A similar reductive conversion of a (p-tolylthio)methyl group into a methyl group was studied.

  DOI：

  10.1021/jo00003a052
• 作为产物：
  描述：

  1,3-benzodithiol-2-ylium tetrafluoroborate 、 在 吡啶 作用下， 反应 1.5h， 生成 2',3',5'-Tri-O-acetyl-N²-(1,3-benzodithiol-2-yl)-N²-methylguanosine
  参考文献：
  名称：

  A convenient method for the synthesis of N2,N2-dimethylguanosine by reductive carbon-sulfur bond cleavage with tributyltin hydride

  摘要：

  A new method for the N-methylation of guanosine is described. The 1,3-benzodithiol-2-yl group was introduced into the 2-amino group of 2',3',5'-tri-O-acetylguanosine (3) and then converted into a methyl group by reductive C-S bond cleavage with tributyltin hydride. This method was also applied to the synthesis of N2,N2-dimethylguanosine. A similar reductive conversion of a (p-tolylthio)methyl group into a methyl group was studied.

  DOI：

  10.1021/jo00003a052

文献信息

• SEKINE, MITSUO;SATOH, TAKAHIKO, J. ORG. CHEM., 56,(1991) N, C. 1224-1227
  作者：SEKINE, MITSUO、SATOH, TAKAHIKO

  DOI：——

  日期：——