N-benzoyl-3'-triisopropylsilyl-5'-keto-8,5'-cyclo-2'-deoxyadenosine | 1403036-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-benzoyl-3'-triisopropylsilyl-5'-keto-8,5'-cyclo-2'-deoxyadenosine
• CAS: 1403036-53-2
• 化学式: C₂₆H₃₃N₅O₄Si
• 分子量: 507.665
• InChiKey: DZMUWXKETHMWRK-JQVVWYNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.23
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-3'-triisopropylsilyl-5'-keto-8,5'-cyclo-2'-deoxyadenosine 在 吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-benzoyl-5'-(1-ethoxyethyl)-8,5'(R)-cyclo-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and Properties of DNA Containing Cyclonucleosides

  摘要：

  Here, we present efficient syntheses of the R and S diastereomers of 8,5'-cyclo-2'-deoxyadenosine and 6,5'-cyclo-2'-deoxyuridine. We incorporated these interesting nucleosides into DNA to study how the cyclo linkage affects the stability of duplex formation.

  DOI：

  10.1080/15257770.2012.716189
• 作为产物：
  描述：

  N-benzoyl-3'-triisopropylsilyl-5'-iodo-2'-deoxyadenosine 在 吡啶 、 selenium(IV) oxide 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 N-benzoyl-3'-triisopropylsilyl-5'-keto-8,5'-cyclo-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and Properties of DNA Containing Cyclonucleosides

  摘要：

  Here, we present efficient syntheses of the R and S diastereomers of 8,5'-cyclo-2'-deoxyadenosine and 6,5'-cyclo-2'-deoxyuridine. We incorporated these interesting nucleosides into DNA to study how the cyclo linkage affects the stability of duplex formation.

  DOI：

  10.1080/15257770.2012.716189

文献信息

• Synthesis and NMR Assignment of the Two Diastereomers of 8,6′-Cyclo-2′,6′-Dideoxyadenosine
  作者：Han Yueh、Ayan Pal、Kenneth Chang、Mark K. Schlegel、Larry W. McLaughlin

  DOI：10.1080/15257770.2013.778997

  日期：2013.1

  We herein present the first synthesis and characterization of the two C5 diastereomers of 8,6-cyclo-2,6-dideoxyadenosine. Starting from commercially available 2-deoxyadenosine, the target cyclonucleosides were synthesized in 11 linear steps. Following a zinc-mediated cyclization reaction to form the seven-membered ring, the stereochemistry of the newly formed chiral center was established using two-dimensional NOESY NMR experiments. [Supplemental materials are available for this article. Go to the publisher's online edition of Nucleosides, Nucleotides & Nucleic Acids for the free supplemental resource.]