(1R,3R,4S,7R)-7-hydroxy-1-hydroxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane | 1174918-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,4S,7R)-7-hydroxy-1-hydroxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: 1-[(1R,3R,4S,7R)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl]pyrimidine-2,4-dione
• CAS: 1174918-19-4
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: KNLNWXXWKDEEFW-OKJYPTKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S,7R)-7-hydroxy-1-hydroxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 吡啶 、 ammonium cerium (IV) nitrate 、 氨 、 碘 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 42.83h， 生成 (1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  [EN] NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS
  [FR] NUCLÉOTIDES ET OLIGONUCLÉOTIDES À CONFORMATION RESTREINTE À FONCTIONNALITÉ NUCLÉOBASE POUR CIBLER DES ACIDES NUCLÉIQUES

  摘要：

  公开号：

  WO2011032034A3
• 作为产物：
  描述：

  (1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane 在 palladium on carbon 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 (1R,3R,4S,7R)-7-hydroxy-1-hydroxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  C5-Alkynyl-Functionalized α-L-LNA: Synthesis, Thermal Denaturation Experiments and Enzymatic Stability

  摘要：

  Major efforts are currently being devoted to improving the binding affinity, target specificity, and enzymatic stability of oligonucleotides used for nucleic acid targeting applications in molecular biology, biotechnology, and medicinal chemistry. One of the most popular strategies toward this end has been to introduce additional modifications to the sugar ring of affinity-inducing conformationally restricted nucleotide building blocks such as locked nucleic acid (LNA). In the preceding article in this issue, we introduced a different strategy toward this end, i.e., C5-functionalization of LNA uridines. In the present article, we extend this strategy to alpha-L-LNA: i.e., one of the most interesting diastereomers of LNA. alpha-L-LNA uridine monomers that are conjugated to small C5-alkynyl substituents induce significant improvements in target affinity, binding specificity, and enzymatic stability relative to conventional alpha-L-LNA. The results from the back-to-back articles therefore suggest that C5-functionalization of pyrimidines is a general and synthetically straightforward approach to modulate biophysical properties of oligonucleotides modified with LNA or other conformationally restricted monomers.

  DOI：

  10.1021/jo5006153

文献信息

• L-Ribo-LNA analogues
  申请人：——

  公开号：US20030087230A1

  公开（公告）日：2003-05-08

  Provided are L-ribo bicyclic nucleotide compounds as well as syntheses of such compounds The nucleoside compounds of the invention are useful in forming oligonucleotides that can produce nucleobase specific duplexes with complementary single stranded and double stranded nucleic acids.

  提供L-核苷酸双环化合物及其合成方法。本发明的核苷酸化合物可用于形成寡核苷酸，可与互补的单链和双链核酸产生核碱基特异性的双链。
• L-RIBO-LNA ANALOGUES
  申请人：Santaris Pharma A/S

  公开号：EP1178999B1

  公开（公告）日：2007-03-14
• [EN] NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS<br/>[FR] NUCLÉOTIDES ET OLIGONUCLÉOTIDES À CONFORMATION RESTREINTE À FONCTIONNALITÉ NUCLÉOBASE POUR CIBLER DES ACIDES NUCLÉIQUES
  申请人：UNIV IDAHO

  公开号：WO2011032034A3

  公开（公告）日：2011-07-21
• US7034133B2
  申请人：——

  公开号：US7034133B2

  公开（公告）日：2006-04-25
• US7053207B2
  申请人：——

  公开号：US7053207B2

  公开（公告）日：2006-05-30