7-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-2-N-dimethylaminomethyleneguanine | 902452-74-8

• 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: 7-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-2-N-dimethylaminomethyleneguanine
• CAS: 902452-74-8
• 化学式: C₃₅H₃₆N₆O₇
• 分子量: 652.707
• InChiKey: JFUIXYSDTLZTDS-GGVMLGSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  48.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  145.55
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  7-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-2-N-dimethylaminomethyleneguanine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 4,5-二氰基咪唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以92%的产率得到7-[3-O-cyanoethoxy(diisopropylamino)phosphino-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-2-N-dimethylaminomethyleneguanine
  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：

  7-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxy-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-N-isobutyrylguanine 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 甲酸 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 7-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-2-N-dimethylaminomethyleneguanine
  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