[(2R)-2-[(2R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-3-oxopropan-2-yl]oxy-2-(2,4-dioxopyrimidin-1-yl)ethyl] benzoate | 1146500-18-6

• 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: [(2R)-2-[(2R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-3-oxopropan-2-yl]oxy-2-(2,4-dioxopyrimidin-1-yl)ethyl] benzoate
• CAS: 1146500-18-6
• 化学式: C₃₇H₃₄N₂O₉
• 分子量: 650.685
• InChiKey: GOPXSCMQXQKKMY-UZNNEEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[(2R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-3-oxopropan-2-yl]oxy-2-(2,4-dioxopyrimidin-1-yl)ethyl] benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 (2R,3R,5R)-3-(4,4'-dimethoxytrityloxymethyl)-2-hydroxy-5-(uracil-1-yl)-1,4-dioxane 、 (2S,3R,5R)-3-(4,4'-dimethoxytrityloxymethyl)-2-hydroxy-5-(uracil-1-yl)-1,4-dioxane
  参考文献：
  名称：

  Oligonucleotides with 1,4-Dioxane-Based Nucleotide Monomers

  摘要：

  An epimeric mixture of H-phosphonates 5R and 5S has been synthesized in three steps from known secouridine 1. Separation of the epimers has been accomplished by RP-HPLC, allowing full characterization and incorporation of monomers X and Y into 9-mer oligonucleotides using H-phosphonates building blocks 5R and 5S, respectively. A single incorporation of either monomer X or monomer Y in the central position of a DNA 9-mer results in decreased thermal affinity toward both DNA and RNA complements (Delta T-m = -3.5 degrees C/-3.5 degrees C for monomer X and Delta T-m = -11.0 degrees C/-6.5 degrees C for monomer Y). CD measurements do not reveal major rearrangements of the duplexes formed, but molecular modeling suggests that local rearrangement of the sugar phosphate backbone and decreased base interactions with neighboring bases might be the origin of the decreased stability of duplexes.

  DOI：

  10.1021/jo300222q
• 作为产物：
  描述：

  2'-O-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine 在 吡啶 、 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 [(2R)-2-[(2R)-1-[bis(4-methoxyphenyl)-phenylmethoxy]-3-oxopropan-2-yl]oxy-2-(2,4-dioxopyrimidin-1-yl)ethyl] benzoate
  参考文献：
  名称：

  Oligonucleotides with 1,4-Dioxane-Based Nucleotide Monomers

  摘要：

  An epimeric mixture of H-phosphonates 5R and 5S has been synthesized in three steps from known secouridine 1. Separation of the epimers has been accomplished by RP-HPLC, allowing full characterization and incorporation of monomers X and Y into 9-mer oligonucleotides using H-phosphonates building blocks 5R and 5S, respectively. A single incorporation of either monomer X or monomer Y in the central position of a DNA 9-mer results in decreased thermal affinity toward both DNA and RNA complements (Delta T-m = -3.5 degrees C/-3.5 degrees C for monomer X and Delta T-m = -11.0 degrees C/-6.5 degrees C for monomer Y). CD measurements do not reveal major rearrangements of the duplexes formed, but molecular modeling suggests that local rearrangement of the sugar phosphate backbone and decreased base interactions with neighboring bases might be the origin of the decreased stability of duplexes.

  DOI：

  10.1021/jo300222q