9-N-vinyl-6-N-dimethoxytrityladenine | 186342-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-N-vinyl-6-N-dimethoxytrityladenine
• 英文别名: N-[bis(4-methoxyphenyl)-phenylmethyl]-9-ethenylpurin-6-amine
• CAS: 186342-08-5
• 化学式: C₂₈H₂₅N₅O₂
• 分子量: 463.539
• InChiKey: KUELEIUBLLTJLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-N-vinyl-6-N-dimethoxytrityladenine 在 三氟乙酸 作用下， 以 氯仿 、 苯 为溶剂， 反应 72.25h， 生成 9-(2-Benzyl-1,2-oxazolidin-5-yl)purin-6-amine
  参考文献：
  名称：

  Leggio, Antonella; Liguori, Angelo; Maiuolo, Loredana, Journal of the Chemical Society. Perkin transactions I, 1997, # 20, p. 3097 - 3099

  摘要：

  DOI：
• 作为产物：
  描述：

  腺嘌呤 在 sodium hydroxide 、 氯化亚砜 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 9-N-vinyl-6-N-dimethoxytrityladenine
  参考文献：
  名称：

  A Novel Class of 4′-Aza Analogues of 2′,3′-Dideoxynucleosides as Potential Anti-HIV Drugs

  摘要：

  The 1,3 dipolar cycloaddition approach represents the most valuable strategy for the preparation of isoxazolidine nucleosides. The latter posses more conformational degrees of freedom than the corresponding dideoxyribosides. Side reactions due to the presence of formaldehyde in the reaction media can be avoided by proper derivatization of the vinyl-nucleobase.

  DOI：

  10.1080/07328319708006219

文献信息

• Synthesis of Two 6-<i>N</i>-Protected 9-<i>N</i>-Vinyladenines as Dipolarophiles in the Synthesis of Modified Nucleosides
  作者：Giselda Giglio、Anna Napoli、Antonella Leggio、Angelo Liguori、Antonio Procopio、Carlo Siciliano、Giovanni Sindona

  DOI：10.1080/00397919608004659

  日期：1996.11

  A new class of potential antiviral drugs is represented by isoxazolidine nucleosides. The paper reports on the synthesis of protected adenines useful as dipolarophiles in the preparation of analogues of dideoxyadenosine by Id-dipolar cycloaddition processes.
• Leggio, Antonella; Liguori, Angelo; Maiuolo, Loredana, Journal of the Chemical Society. Perkin transactions I, 1997, # 20, p. 3097 - 3099
  作者：Leggio, Antonella、Liguori, Angelo、Maiuolo, Loredana、Napoli, Anna、Procopio, Antonio、Siciliano, Carlo、Sindona, Giovanni

  DOI：——

  日期：——
• A Novel Class of 4′-Aza Analogues of 2′,3′-Dideoxynucleosides as Potential Anti-HIV Drugs
  作者：Antonella Leggio、Angelo Liguori、Antonio Procopio、Carlo Siciliano、Giovanni Sindona

  DOI：10.1080/07328319708006219

  日期：1997.7

  The 1,3 dipolar cycloaddition approach represents the most valuable strategy for the preparation of isoxazolidine nucleosides. The latter posses more conformational degrees of freedom than the corresponding dideoxyribosides. Side reactions due to the presence of formaldehyde in the reaction media can be avoided by proper derivatization of the vinyl-nucleobase.