1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-dimethylmalonate)-β-D-pentofuranosyl>thymine | 158774-94-8

• 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: 1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-dimethylmalonate)-β-D-pentofuranosyl>thymine
• 英文别名: dimethyl 2-[(2S,3S,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-(nitromethyl)oxolan-3-yl]propanedioate
• CAS: 158774-94-8
• 化学式: C₄₂H₅₁N₃O₁₂Si
• 分子量: 817.965
• InChiKey: PXEZCWWLXBGGRX-XNBBIPQXSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  58
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-dimethylmalonate)-β-D-pentofuranosyl>thymine 在 溶剂黄146 作用下， 以94%的产率得到1-<2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-dimethylmalonate)-β-D-pentofuranosyl>thymine
  参考文献：
  名称：

  New synthesis of 3′--substituted-3′-nitromethyl-ribo-thymidines

  摘要：

  The 3'-exo-nitromethylene-function in ribo-thymidine, as in 3, has been used for the first lime as a general intermediate in the Michael addition reaction to give varieties of 3'-($) under bar C-subsituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.

  DOI：

  10.1016/s0040-4020(01)86711-9
• 作为产物：
  描述：

  1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-C-exo-nitromethylene-β-D-pentofuranosyl>thymine 、 丙二酸二甲酯 在 potassium tert-butylate 作用下， 反应 4.0h， 以81%的产率得到1-<5-O-(4-monomethoxytrityl)-2-(R)-O-t-butyldimethylsilyl-3-deoxy-3-C-nitromethyl-3-(R)-C-(α-dimethylmalonate)-β-D-pentofuranosyl>thymine
  参考文献：
  名称：

  New synthesis of 3′--substituted-3′-nitromethyl-ribo-thymidines

  摘要：

  The 3'-exo-nitromethylene-function in ribo-thymidine, as in 3, has been used for the first lime as a general intermediate in the Michael addition reaction to give varieties of 3'-($) under bar C-subsituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.

  DOI：

  10.1016/s0040-4020(01)86711-9