N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine | 325771-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine
• CAS: 325771-82-2
• 化学式: C₂₅H₂₅N₃O₆
• 分子量: 463.49
• InChiKey: ACNCFZVNTZPDPJ-VSKRKVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  124.86
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-(4S)-O-((β-cyanoethyl-N,N'-diisopropylphosphoramidite)oxy)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine
  参考文献：
  名称：

  Pyrrolidino-DNA

  摘要：

  We synthesized pyrrolidino-C-nucleosides, incorporated them into oligodeoxynucleotides and investigated their pairing properties. The thermal duplex and triplex stabilities were measured. While triplex formation is destabilized in the case of pyrrolidino-pseudo-U and -T, pyrrolidino-pseudo-iso-C leads to an increase of the T-m value for third strand dissociation. Duplexes Lire destabilized with all pyrrolidino-C-nucleosides.

  DOI：

  10.1081/ncn-120022832
• 作为产物：
  描述：

  1-Pyrrolidinecarboxylic acid,3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-1-methyl-2,4-dioxo-5-pyrimidinyl)-, phenylmethyl ester, (2R,5R)- 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine
  参考文献：
  名称：

  Pyrrolidino-DNA

  摘要：

  We synthesized pyrrolidino-C-nucleosides, incorporated them into oligodeoxynucleotides and investigated their pairing properties. The thermal duplex and triplex stabilities were measured. While triplex formation is destabilized in the case of pyrrolidino-pseudo-U and -T, pyrrolidino-pseudo-iso-C leads to an increase of the T-m value for third strand dissociation. Duplexes Lire destabilized with all pyrrolidino-C-nucleosides.

  DOI：

  10.1081/ncn-120022832

文献信息

• Synthesis of Pyrrolidine <i>C</i>-Nucleosides via Heck Reaction
  作者：Adrian Häberli、Christian J. Leumann

  DOI：10.1021/ol007029s

  日期：2001.2.1

  [GRAPHICS]A novel method for the synthesis of pyrrolidine C-nucleosides has keen developed, The key step of the synthesis is the palladium(0)-mediated coupling of a disubstituted N-protected 2-pyrroline and 5-iodouracil. C-Nucleoside 14 and its N-methyl derivative 15 can easily be convened to the corresponding phosphoramidite building blocks for DNA synthesis.