(2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester | 340981-80-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS: 340981-80-8
• 化学式: C₂₆H₂₅N₃O₇
• 分子量: 491.5
• InChiKey: GZPFRTPLXYLHOI-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 palladium on activated charcoal 锂硼氢 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙酸乙酯 为溶剂， 生成 1-{(3R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-yl}-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Pyrrolidine Nucleic Acids:  DNA/PNA Oligomers with 2-Hydroxy/Aminomethyl- 4-(thymin-1-yl)pyrrolidine-N-acetic acid

  摘要：

  [GRAPHICS]Synthesis of pyrrolidine-based chiral positively charged DNA analogues is reported, The synthesis of (2S,4S) and (2R,4R) thymin-1-ylpyrrolidine-N-acetic acid, its site specific incorporation in PNA:DNA chimera and PNA, and the study of their binding properties with complementary DNA/RNA sequences is presented.

  DOI：

  10.1021/ol0069655
• 作为产物：
  描述：

  N-3-benzoylthymine 、 N-苄氧羰基-反式-4-羟基-D-脯氨酸甲酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以68%的产率得到(2R,4R)-4-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
  参考文献：
  名称：

  Pyrrolidine Nucleic Acids:  DNA/PNA Oligomers with 2-Hydroxy/Aminomethyl- 4-(thymin-1-yl)pyrrolidine-N-acetic acid

  摘要：

  [GRAPHICS]Synthesis of pyrrolidine-based chiral positively charged DNA analogues is reported, The synthesis of (2S,4S) and (2R,4R) thymin-1-ylpyrrolidine-N-acetic acid, its site specific incorporation in PNA:DNA chimera and PNA, and the study of their binding properties with complementary DNA/RNA sequences is presented.

  DOI：

  10.1021/ol0069655

文献信息

• Pyrrolidine PNA-DNA Chimeric Oligonucleotides with Extended Backbone
  作者：Vaijayanti A. Kumar、Meena

  DOI：10.1081/ncn-120022746

  日期：2003.10

  Cis-D-2-hydroxy-4-thymin-1-yl-pyrrolidine propionic acid unit is used to make PNA-DNA dimer block that is incorporated in DNA sequences at selected positions. Since the amide linkage is shorter than phosphodiester linkage, insertion of an extra atom in the backbone with amide linkage seems to be better accommodated for internucleotide distance-complementarity.