(S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide | 1100358-76-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide
• 英文别名: tert-butyl-[[(2S)-1-oxo-1lambda4-selenolan-2-yl]methoxy]-diphenylsilane；tert-butyl-[[(2S)-1-oxo-1λ4-selenolan-2-yl]methoxy]-diphenylsilane
• CAS: 1100358-76-6
• 化学式: C₂₁H₂₈O₂SeSi
• 分子量: 419.498
• InChiKey: CXDJCUKRFFBPSN-VEXWJQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide 、 胸腺嘧啶 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15%的产率得到D-5'-tert-butyldiphenylsilyl-2',3'-dideoxy-4'-selenothymidine
  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 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以98%的产率得到(S)-2-(tert-butyldiphenylsilyloxymethyl)dihydroselenofuran-1-oxide
  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