3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one | 644962-78-7

• 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: 3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one
• 英文别名: 3-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-6-methylfuro[2,3-d]pyrimidin-2-one
• CAS: 644962-78-7
• 化学式: C₃₃H₃₂N₂O₇
• 分子量: 568.626
• InChiKey: VNUJSHVQSNNLDQ-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-(5'-O-二甲氧基三苯甲基)-Β-D-2-脱氧呋喃核糖)-6-甲基吡咯[2,3-D]PYRIMIDIN-2-ONE
  参考文献：
  名称：

  The 6-Methoxymethyl Derivative Of Pyrrolo-Dc For Selective Fluorometric Detection Of Guanosine-Containing Sequences

  摘要：

  The beta-cyanoethyl phosphosphoramidite derivatives of 6-methyl- and 6-methoxymethyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one have been synthesized. These monomers have been employed for oligodeoxynucleolide synthesis to evaluate their effect on duplex stability and ability to fluorometrically report on hybridization. The structurally conservative 6-methroxymethyl-substitution results in a pyrrolocylidine that is stabilizing toward hybrid formation (Delta Tm = +1.3 degrees C) whereas the known 6-methylpyrrolocytidine is destabilizing (Delta Tm = -4.7 degrees C), in the sequence examined. The 6-methoxymethylpyrrolocytidine retains excellent mismatch discrimination and its fluorescence is selectively quenched when hybridized to a match oligodeoxynucleotide sequence. The quenching of fluorescence for an internal position is approximately three-fold, whereas a terminal position (5'-end or 3'-end) experienced approximately two-fold decrease in the fluorescence intensity.

  DOI：

  10.1080/15257770701489839
• 作为产物：
  描述：

  碘苷 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides

  摘要：

  Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.108

文献信息

• Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides
  作者：David A. Berry、Kee-Yong Jung、Dean S. Wise、Anthony D. Sercel、William H. Pearson、Hugh Mackie、John B. Randolph、Robert L. Somers

  DOI：10.1016/j.tetlet.2004.01.108

  日期：2004.3

  Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.
• The 6-Methoxymethyl Derivative Of Pyrrolo-Dc For Selective Fluorometric Detection Of Guanosine-Containing Sequences
  作者：Robert H. E. Hudson、Arash Ghorbani Choghamarani

  DOI：10.1080/15257770701489839

  日期：2007.11.26

  The beta-cyanoethyl phosphosphoramidite derivatives of 6-methyl- and 6-methoxymethyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one have been synthesized. These monomers have been employed for oligodeoxynucleolide synthesis to evaluate their effect on duplex stability and ability to fluorometrically report on hybridization. The structurally conservative 6-methroxymethyl-substitution results in a pyrrolocylidine that is stabilizing toward hybrid formation (Delta Tm = +1.3 degrees C) whereas the known 6-methylpyrrolocytidine is destabilizing (Delta Tm = -4.7 degrees C), in the sequence examined. The 6-methoxymethylpyrrolocytidine retains excellent mismatch discrimination and its fluorescence is selectively quenched when hybridized to a match oligodeoxynucleotide sequence. The quenching of fluorescence for an internal position is approximately three-fold, whereas a terminal position (5'-end or 3'-end) experienced approximately two-fold decrease in the fluorescence intensity.