1-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-α-L-ribofuranosyl)thymine | 902452-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-α-L-ribofuranosyl)thymine
• 英文别名: [(1S,3R,4S,7R)-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-7-phenylmethoxy-2,5-dioxabicyclo[2.2.1]heptan-1-yl]methyl methanesulfonate
• CAS: 902452-67-9
• 化学式: C₁₉H₂₂N₂O₈S
• 分子量: 438.458
• InChiKey: IRULAYAQKRRXDM-MGTHKWJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-α-L-ribofuranosyl)thymine 在 palladium dihydroxide 吡啶 、 甲酸铵 、 N,N-二异丙基乙胺 、 苯甲醇钠 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 8.5h， 生成 1-[3-O-acetyl-5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-α-L-ribofuranosyl]-5-methyl-4-(1,2,4-triazol-1-yl)-2-oxypyrimidine
  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：

  3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-1,2-O-isopropylidene-β-L-threo-pentofuranose 在 吡啶 、 盐酸 、 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 49.5h， 生成 1-(3-O-benzyl-5-O-methanesulfonyl-2-O,4-C-methylene-α-L-ribofuranosyl)thymine
  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

文献信息

• Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine
  作者：Alexei A. Koshkin

  DOI：10.1016/j.tet.2006.04.016

  日期：2006.6

  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.