(2S,3S,5R)-2-Benzyloxymethyl-5-[3-(4-methoxy-benzyloxymethyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-carbaldehyde | 192652-90-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (2S,3S,5R)-2-Benzyloxymethyl-5-[3-(4-methoxy-benzyloxymethyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-carbaldehyde
• CAS: 192652-90-7
• 化学式: C₂₇H₃₀N₂O₇
• 分子量: 494.544
• InChiKey: WUVGQCPQPQSODQ-QLBJFCOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  97.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  草酸醛 、 (2S,3S,5R)-2-Benzyloxymethyl-5-[3-(4-methoxy-benzyloxymethyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-carbaldehyde 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以49%的产率得到1-[(2R,4R,5S)-5-Benzyloxymethyl-4-(1H-imidazol-2-yl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: the effect of triazole- and imidazole-modified backbones on DNA/RNA duplex stability

  摘要：

  Thymidine dinucleotide analogs with imidazole-derived backbones (III and IV) were synthesized. These modified dimeric building blocks were incorporated into oligodeoxyribonucleotides. The hybridization affinity of the modified oligonucleotides for RNA complements was determined and compared to the corresponding olefinic modifications I and II. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00270-9
• 作为产物：
  描述：

  1-[(氯甲氧基)甲基]-4-甲氧基苯 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 、 乙腈 为溶剂， 反应 40.0h， 生成 (2S,3S,5R)-2-Benzyloxymethyl-5-[3-(4-methoxy-benzyloxymethyl)-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-carbaldehyde
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: the effect of triazole- and imidazole-modified backbones on DNA/RNA duplex stability

  摘要：

  Thymidine dinucleotide analogs with imidazole-derived backbones (III and IV) were synthesized. These modified dimeric building blocks were incorporated into oligodeoxyribonucleotides. The hybridization affinity of the modified oligonucleotides for RNA complements was determined and compared to the corresponding olefinic modifications I and II. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00270-9