bis(2'-O,3'-O-isopropylidene-5'-deoxyuridine)-5',5'-diselenide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: bis(2'-O,3'-O-isopropylidene-5'-deoxyuridine)-5',5'-diselenide
• 英文别名: bis-(5'-deoxy-2',3'-O-isopropylidene-uridine)-5',5'-diselenide；1-[(3aR,4R,6S,6aS)-6-[[[(3aR,4R,6S,6aS)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyldiselanyl]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione
• 化学式: C₂₄H₃₀N₄O₁₀Se₂
• 分子量: 692.443
• InChiKey: YHIBKBAKVBPGDJ-LSRAZJPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3'-O-isopropylidene-5'-O-tosyluridine 在 [tetrabutylammonium]2[WSe4] 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以74%的产率得到bis(2'-O,3'-O-isopropylidene-5'-deoxyuridine)-5',5'-diselenide
  参考文献：
  名称：

  Novel chalcogenides of thymidine and uridine: synthesis, properties and applications

  摘要：

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.02.035

文献信息

• NEW 3′-DEOXYTHYMIDINES BEARING A NUCLEOPHILIC 3′-SUBSTITUENT
  作者：Anatoly M. Belostotskii、Helen Keren-Yeshuah、Jael Lexner、Alfred Hassner

  DOI：10.1081/ncn-100001439

  日期：2001.2.26

  New potential cancer-driven as well as HIV-driven nucleoside heteroanalogs, such as 3'-thio- and 3'- as well as 5'-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for-3'-alpha -alkylthiothymidines.
• Novel chalcogenides of thymidine and uridine: synthesis, properties and applications
  作者：Kirubakaran Sivapriya、Perumal Suguna、S. Shubashree、Perali Ramu Sridhar、Srinivasan Chandrasekaran

  DOI：10.1016/j.carres.2007.02.035

  日期：2007.7

  A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides. (C) 2007 Elsevier Ltd. All rights reserved.