α-D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-seleno-N4-benzoylcytidine | 1100358-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-seleno-N4-benzoylcytidine
• 英文别名: N-[1-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]selenolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 1100358-95-9
• 化学式: C₃₂H₃₅N₃O₃SeSi
• 分子量: 616.694
• InChiKey: RUWUWWMFZSIEJR-SVEHJYQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-seleno-N4-benzoylcytidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成
  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：

  N4-苯甲酰基胞嘧啶 、 (S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide 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10%的产率得到β-D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-seleno-N4-benzoylcytidine
  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