1-(1-butyn-4-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose | 1451958-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(1-butyn-4-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose
• CAS: 1451958-64-7
• 化学式: C₃₀H₃₂O₅
• 分子量: 472.581
• InChiKey: PBNAWNSVVJUAEY-YTCPBCGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(1-butyn-4-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以97%的产率得到1-(1-butyn-4-yl)-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose
  参考文献：
  名称：

  Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3-triazole nucleobases linked via a two atom-length spacer

  摘要：

  Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various azides gave the corresponding triazolylated oligonucleotides, triplex-forming ability of these synthetic oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. It was found that nucleobases containing 2-(1-m-carbonylaminophenyl-1,2,3-triazol-4-yl)ethyl units likely interacted with A of a TA base pair in a parallel triplex DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.034
• 作为产物：
  描述：

  ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 1-(1-butyn-4-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose
  参考文献：
  名称：

  Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3-triazole nucleobases linked via a two atom-length spacer

  摘要：

  Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various azides gave the corresponding triazolylated oligonucleotides, triplex-forming ability of these synthetic oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. It was found that nucleobases containing 2-(1-m-carbonylaminophenyl-1,2,3-triazol-4-yl)ethyl units likely interacted with A of a TA base pair in a parallel triplex DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.034