2'-deoxy-3',5'-bis-O-triphenylmethyluridine | 1140622-58-7

• 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: 2'-deoxy-3',5'-bis-O-triphenylmethyluridine
• 英文别名: 5',3'-di-O-trityl-2'-deoxyuridine；1-[(2R,4S,5R)-4-trityloxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1140622-58-7
• 化学式: C₄₇H₄₀N₂O₅
• 分子量: 712.845
• InChiKey: KCKRRKIOURUDKV-RXAPTJIMSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3',5'-bis-O-triphenylmethyluridine 、 苯甲醇 在 copper(II) sulfate 作用下， 以 xylene 为溶剂， 反应 5.0h， 以49%的产率得到2-脱氧尿苷
  参考文献：
  名称：

  保护基团转移：通过醚交换作用去除Tr和Tbdms基团的不寻常方法

  摘要：

  在由Cu + 2，Fe + 2或Ni + 2的无水硫酸盐介导的过程中，三苯甲基（Tr）基团在5'-O-Tr-2'-脱氧核苷分子之间进行转移（转移醚化或歧化）得到3′，5′-双-O-Tr和3′-O-Tr产物的混合物。如果反应介质中存在苯甲醇，则会导致脱三苯甲基化并同时形成苯甲基三苯甲基醚。5'-O-TBDMS-2'-脱氧核苷中叔丁基二甲基甲硅烷基（TBDMS）的行为完全相同。以前没有在O-Tr和O-TBDMS组中观察到这种类型的转醚化作用。

  DOI：

  10.1080/15257770802257846
• 作为产物：
  描述：

  2-脱氧尿苷 、 三苯基氯甲烷 以 吡啶 为溶剂， 以38%的产率得到2'-deoxy-3',5'-bis-O-triphenylmethyluridine
  参考文献：
  名称：

  In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues

  摘要：

  Following up on a hit that was identified in a large scale cell-based antiviral screening effort, a series of triphenylmethyl alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against the dengue virus (DENV) and the yellow fever virus (YFV). Hereto, trityl moieties were attached at various positions of the sugar ring combined with subtle variations of the heterocyclic base. Several triphenylmethyl modified nucleosides were uncovered being endowed with submicromolar in vitro antiviral activity against the YFV. The most selective inhibitor in this series was 3',5'-bis-O-tritylated-5-chlorouridine (1b) affording a selectivity index of over 90, whereas the 3',5'-bis-O-tritylated inosine congener (5b) displayed the highest activity, but proved more toxic. The finding of these lipophilic structures being endowed with high antiviral activity for flaviviruses, should stimulate the interest for further structure-activity research. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.034

文献信息

• In search of flavivirus inhibitors: Evaluation of different tritylated nucleoside analogues
  作者：Grégory Chatelain、Yannick Debing、Tine De Burghgraeve、Joanna Zmurko、Milind Saudi、Jef Rozenski、Johan Neyts、Arthur Van Aerschot

  DOI：10.1016/j.ejmech.2013.04.034

  日期：2013.7

  Following up on a hit that was identified in a large scale cell-based antiviral screening effort, a series of triphenylmethyl alkylated nucleoside analogues were synthesized and evaluated for their in vitro antiviral activities against the dengue virus (DENV) and the yellow fever virus (YFV). Hereto, trityl moieties were attached at various positions of the sugar ring combined with subtle variations of the heterocyclic base. Several triphenylmethyl modified nucleosides were uncovered being endowed with submicromolar in vitro antiviral activity against the YFV. The most selective inhibitor in this series was 3',5'-bis-O-tritylated-5-chlorouridine (1b) affording a selectivity index of over 90, whereas the 3',5'-bis-O-tritylated inosine congener (5b) displayed the highest activity, but proved more toxic. The finding of these lipophilic structures being endowed with high antiviral activity for flaviviruses, should stimulate the interest for further structure-activity research. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Protecting Groups Transfer: Unusual Method of Removal of Tr and Tbdms Groups by Transetherification
  作者：Nadia L. D. Cabral、Luciano J. Hoeltgebaum Thiessen、Bogdan Doboszewski

  DOI：10.1080/15257770802257846

  日期：2008.8.11

  The triphenylmethyl (Tr) group undergoes a transfer (transetherification or disproportionation) between the molecules of 5′-O-Tr-2′-deoxynucleosides in a process mediated by anhydrous sulfates of Cu+2, Fe+2, or Ni+2 to yield mixtures of 3′,5′-bis-O-Tr and 3′-O-Tr products. If phenylmethanol is present in a reaction medium, detritylation results with concomitant formation of phenylmethyl triphenylmethyl

  在由Cu + 2，Fe + 2或Ni + 2的无水硫酸盐介导的过程中，三苯甲基（Tr）基团在5'-O-Tr-2'-脱氧核苷分子之间进行转移（转移醚化或歧化）得到3′，5′-双-O-Tr和3′-O-Tr产物的混合物。如果反应介质中存在苯甲醇，则会导致脱三苯甲基化并同时形成苯甲基三苯甲基醚。5'-O-TBDMS-2'-脱氧核苷中叔丁基二甲基甲硅烷基（TBDMS）的行为完全相同。以前没有在O-Tr和O-TBDMS组中观察到这种类型的转醚化作用。