3-Benzyloxymethyl-1-[(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-(3-oxo-butyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione | 192564-24-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 3-Benzyloxymethyl-1-[(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-(3-oxo-butyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 192564-24-2
• 化学式: C₃₇H₄₄N₂O₆Si
• 分子量: 640.852
• InChiKey: DVYVPNGKRUKWSE-OUYGKKDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  46.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-Benzyloxymethyl-1-[(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-(3-oxo-butyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 苯 为溶剂， -78.0~80.0 ℃ 、100.0 kPa 条件下， 反应 89.5h， 生成
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2
• 作为产物：
  描述：

  3-Benzyloxymethyl-1-[(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-but-1-enyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到3-Benzyloxymethyl-1-[(2R,4S,5R)-4-(tert-butyl-diphenyl-silanyloxy)-5-(3-oxo-butyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2