2-bromo-3,9-dihydro-6-methyl-9-oxo-3-(β-D-ribofuranosyl)-5H-imidazo[1,2-a]purine | 1404304-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3,9-dihydro-6-methyl-9-oxo-3-(β-D-ribofuranosyl)-5H-imidazo[1,2-a]purine
• CAS: 1404304-91-1
• 化学式: C₁₃H₁₄BrN₅O₅
• 分子量: 400.189
• InChiKey: ZIKFXNMYFOACCX-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137.9
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-bromo-3,9-dihydro-6-methyl-9-oxo-3-(β-D-ribofuranosyl)-5H-imidazo[1,2-a]purine 、 乙酸酐 以 吡啶 为溶剂， 以89%的产率得到2-bromo-3,9-dihydro-6-methyl-9-oxo-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  2-Methylwyosine, a Nucleoside With Restricted Anti Conformation in the East Region Enforced by Nucleobase Moiety Modification: Synthesis and Conformational Analysis by NMR and Molecular Dynamics

  摘要：

  We synthesized a new 2-methyl derivative of wyosine using a multistep procedure starting from guanosine. We examined different synthetic paths and optimized the conditions for each step. Based on MD calculations and analysis of the (3)J(HH) and J(C1'H1') of the ribose moiety, we discovered that the sugar part adopted conformation specific for the East region rarely occurring in solution. This unusual conformational preference is probably due to steric repulsions between the methyl group at position 2 and the 5'-CH2OH group. We observed that N-glycosidic bond stability weakened 14-fold upon the introduction of the methyl group in position 2 compared with wyosine.

  DOI：

  10.1080/15257770.2012.724133
• 作为产物：
  描述：

  鸟苷 在 溴 、 sodium hydride 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 2-bromo-3,9-dihydro-6-methyl-9-oxo-3-(β-D-ribofuranosyl)-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  2-Methylwyosine, a Nucleoside With Restricted Anti Conformation in the East Region Enforced by Nucleobase Moiety Modification: Synthesis and Conformational Analysis by NMR and Molecular Dynamics

  摘要：

  We synthesized a new 2-methyl derivative of wyosine using a multistep procedure starting from guanosine. We examined different synthetic paths and optimized the conditions for each step. Based on MD calculations and analysis of the (3)J(HH) and J(C1'H1') of the ribose moiety, we discovered that the sugar part adopted conformation specific for the East region rarely occurring in solution. This unusual conformational preference is probably due to steric repulsions between the methyl group at position 2 and the 5'-CH2OH group. We observed that N-glycosidic bond stability weakened 14-fold upon the introduction of the methyl group in position 2 compared with wyosine.

  DOI：

  10.1080/15257770.2012.724133