(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane | 1052725-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 1-[(1S,3R,4R,6R,7S)-6-(hydroxymethyl)-7-phenylmethoxy-1-(phenylmethoxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1052725-31-1
• 化学式: C₂₆H₂₈N₂O₇
• 分子量: 480.518
• InChiKey: YHTFUISLEOGGAA-ZQWZWNDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 在 palladium hydroxide - carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 96.0h， 以65%的产率得到(1S,3R,4R,6R,7S)-1,6-bis(hydroxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis of 6′-Branched Locked Nucleic Acid by a Radical TEMPO-Scavanged Stereoselective Mercury Cyclization

  摘要：

  A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This Compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.

  DOI：

  10.1021/jo801081t
• 作为产物：
  描述：

  (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 以83%的产率得到(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis of 6′-Branched Locked Nucleic Acid by a Radical TEMPO-Scavanged Stereoselective Mercury Cyclization

  摘要：

  A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This Compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.

  DOI：

  10.1021/jo801081t

文献信息

• Synthesis of 6′-Branched Locked Nucleic Acid by a Radical TEMPO-Scavanged Stereoselective Mercury Cyclization
  作者：Gerald Enderlin、Poul Nielsen

  DOI：10.1021/jo801081t

  日期：2008.9.1

  A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This Compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.