(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-7-yl)-2,5-dioxabicyclo[2.2.1]heptane | 709641-80-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-7-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 7-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine
• CAS: 709641-80-5
• 化学式: C₂₃H₂₇N₅O₈S
• 分子量: 533.562
• InChiKey: KNUVFWZSFLXTCT-BPVRBSMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  163.73
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-7-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-(3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine
  参考文献：
  名称：

  Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine

  摘要：

  The method for scaled-up production of alpha-L-LNA phosphoramidite building blocks containing thymine and 5-methylcytosine nucleobases is described. Binding properties of pyrimidine TFOs modified with alpha-L-LNA are reported. In contrast to LNA TFOs, the fully modified a-L-LNA forms a stable triplex with a model DNA duplex. Pyrimidine DNA/LNA/alpha-L-LNA chimeras also efficiently hybridize with a model DNA duplex in the parallel mode. LNA nucleoside containing unnatural N-7-glycosylated guanine (LNA-(7) G) was synthesized by a convergent method and incorporated into LNA oligonucleotides. The triplex-forming alternating DNA/LNA oligonucleotides containing a single LNA-(7) G modification instead of internal LNA-mC demonstrate improved pH-dependent properties. The single LNA-(7) G modification can also discriminatively reduce competitive binding of TFOs to natural nucleic acids in the antiparallel duplex mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.016
• 作为产物：
  描述：

  N-(6,7-二氢-6-氧代-1H-嘌呤-2-基)-2-甲基丙酰胺 在 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 20.0h， 生成 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(2-N-isobutyrylguanin-7-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine

  摘要：

  The method for scaled-up production of alpha-L-LNA phosphoramidite building blocks containing thymine and 5-methylcytosine nucleobases is described. Binding properties of pyrimidine TFOs modified with alpha-L-LNA are reported. In contrast to LNA TFOs, the fully modified a-L-LNA forms a stable triplex with a model DNA duplex. Pyrimidine DNA/LNA/alpha-L-LNA chimeras also efficiently hybridize with a model DNA duplex in the parallel mode. LNA nucleoside containing unnatural N-7-glycosylated guanine (LNA-(7) G) was synthesized by a convergent method and incorporated into LNA oligonucleotides. The triplex-forming alternating DNA/LNA oligonucleotides containing a single LNA-(7) G modification instead of internal LNA-mC demonstrate improved pH-dependent properties. The single LNA-(7) G modification can also discriminatively reduce competitive binding of TFOs to natural nucleic acids in the antiparallel duplex mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.016