N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl]-9H-purin-6-yl}-benzamide | 726186-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl]-9H-purin-6-yl}-benzamide
• CAS: 726186-36-3
• 化学式: C₂₄H₃₃N₅O₄Si
• 分子量: 483.643
• InChiKey: LXERCLVHBNMIBO-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl]-9H-purin-6-yl}-benzamide 在 吡啶 、 四丁基氟化铵 、 苯甲基-2-磺酰三硝基三氮唑 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 51.5h， 生成 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-ylmethyl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-5-(6-amino-purin-9-ylmethyl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Homo-N-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity

  摘要：

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.

  DOI：

  10.1021/ja049865t
• 作为产物：
  描述：

  2,5-Anhydro-1,3-dideoxy-1-(N-benzoyladenin-9-yl)-D-allitol 在 吡啶 、 咪唑 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 N-{9-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl]-9H-purin-6-yl}-benzamide
  参考文献：
  名称：

  Homo-N-oligonucleotides (N1/N9−C1‘ Methylene Bridge Oligonucleotides):  Nucleic Acids with Left-Handed Helicity

  摘要：

  Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dinners have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homotype dsDNA. Homo-type dinners and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.

  DOI：

  10.1021/ja049865t