(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 | 1052725-28-6

• 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)-7-benzyloxy-1-benzyloxymethyl-6-(2,2,6,6-tetramethylpiperidin-1-yl)oxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 5-methyl-1-[(1S,3R,4R,6R,7S)-7-phenylmethoxy-1-(phenylmethoxymethyl)-6-[(2,2,6,6-tetramethylpiperidin-1-yl)oxymethyl]-2,5-dioxabicyclo[2.2.1]heptan-3-yl]pyrimidine-2,4-dione
• CAS: 1052725-28-6
• 化学式: C₃₅H₄₅N₃O₇
• 分子量: 619.758
• InChiKey: ZGIFIJBIYKZHSF-ZYHPLVGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 (1R,3R,4R,6S,7S)-7-benzyloxy-1-benzyloxymethyl-6-bromomercuriomethyl-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以77%的产率得到(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
  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.