D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-selenouridine | 1100358-82-4

• 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: D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-selenouridine
• CAS: 1100358-82-4
• 化学式: C₂₅H₃₀N₂O₃SeSi
• 分子量: 513.57
• InChiKey: YRRSDYYLNVDBHN-HSTJUUNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.09
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-selenouridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以93%的产率得到D-2',3'-dideoxy-4'-selenouridine
  参考文献：
  名称：

  Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

  摘要：

  On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2', 3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, D-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se-2 and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.034
• 作为产物：
  描述：

  (S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide 、 尿嘧啶 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 甲苯 、 二氯甲烷 为溶剂， 反应 16.0h， 以13%的产率得到D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-selenouridine
  参考文献：
  名称：

  Design and synthesis of novel 2′,3′-dideoxy-4′-selenonucleosides as potential antiviral agents

  摘要：

  On the basis of potent anti-HIV activity of 2',3'-dideoxynucleosides (ddNs), their bioisosteric analogues, 2', 3'-dideoxy-4'-selenonucleosides (4'-seleno-ddNs) were first synthesized from a chiral template, D-glutamic acid using stereoselective ring-closure reaction of the dimesylate with Se-2 and Pummerer type condensation of the selenoxide with nucleobases as key steps. X-ray crystallographic analysis indicated that 4'-seleno-ddNs adopted the same C2'-endo/C3'-exo (South) conformation as anti-HIV active ddNs, but did not show anti-HIV activity, indicating that RT seems to prefer the C2'-exo/C3'-endo (North) conformation on binding with their triphosphates. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.034