(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethylpyrrolidine | 325771-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethylpyrrolidine
• 英文别名: 5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1H-pyrimidine-2,4-dione
• CAS: 325771-79-7
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: GDUQXXRGHHXTBO-QYNIQEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethylpyrrolidine 在 吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(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：

  FMOC-反式-3-羟基-L-脯氨酸 在 palladium on activated charcoal 、 palladium diacetate 哌啶 、 咪唑 、 N-氯代丁二酰亚胺 、 三正丁胺 、 三苯胂 、 dimethyl sulfide borane 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 四丁基氟化铵 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 89.33h， 生成 (2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethylpyrrolidine
  参考文献：
  名称：

  Synthesis of Pyrrolidine C-Nucleosides via Heck Reaction

  摘要：

  [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.

  DOI：

  10.1021/ol007029s

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.
• Pyrrolidino-DNA
  作者：Adrian Häberli、Alain Mayer、Christian J. Leumann

  DOI：10.1081/ncn-120022832

  日期：2003.10

  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.