(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-methanesulfonyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane | 1052725-47-9

• 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-6-methanesulfonyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS: 1052725-47-9
• 化学式: C₂₇H₃₀N₂O₉S
• 分子量: 558.609
• InChiKey: JAWOODLYEIDUFT-IFXLZMBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  135.15
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-methanesulfonyloxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以89%的产率得到(1S,3R,4R,6R,7S)-6-azidomethyl-7-benzyloxy-1-benzyloxymethyl-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-3-(thymin-1-yl)-6-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 、 甲基磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以90%的产率得到(1S,3R,4R,6R,7S)-7-benzyloxy-1-benzyloxymethyl-6-methanesulfonyloxymethyl-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