[(2R,3S,5R)-2-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate | 188944-87-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
• CAS: 188944-87-8
• 化学式: C₂₇H₃₆N₇O₁₂P
• 分子量: 681.596
• InChiKey: JJGIDGYKTLDHEY-VMLZCNNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  238
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 吡啶 为溶剂， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
  参考文献：
  名称：

  New Stereospecific Method of Synthesis of [Sp]- and [Rp]-Dinucleoside-(3',5') Methanephosphonates

  摘要：

  Using a stereoretentive reaction between diastereomerically pure 5'-O-DMT-(N-protected) nucleoside 3'-O-(Se-methyl methanephosphonoselenolate)s and 3'-O-acetyl-(N-protected) nucleosides, diastereomerically pure dinucleoside-(3',5') methanephosphonates as well as ''all-Rp'' and ''all-Sp'' trimers, tetramers, and pentamers were synthesized.

  DOI：

  10.1021/jo00099a001
• 作为产物：
  描述：

  (Rp)-5'-O-DMT-thymidine-3'-O-(Se-methyl methanephosphonoselenolate) 在 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 吡啶 为溶剂， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] acetate
  参考文献：
  名称：

  New Stereospecific Method of Synthesis of [Sp]- and [Rp]-Dinucleoside-(3',5') Methanephosphonates

  摘要：

  Using a stereoretentive reaction between diastereomerically pure 5'-O-DMT-(N-protected) nucleoside 3'-O-(Se-methyl methanephosphonoselenolate)s and 3'-O-acetyl-(N-protected) nucleosides, diastereomerically pure dinucleoside-(3',5') methanephosphonates as well as ''all-Rp'' and ''all-Sp'' trimers, tetramers, and pentamers were synthesized.

  DOI：

  10.1021/jo00099a001