(1S,3R,4R,6R,7S)-1,6-bis(hydroxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane | 1052725-44-6

• 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)-1,6-bis(hydroxymethyl)-7-hydroxy-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 1-[(1R,3R,4R,6R,7S)-7-hydroxy-1,6-bis(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1052725-44-6
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: IMWMTPRHQZLAFD-RCYRUSIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  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