Phosphorous acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,6-dichloro-phenyl) ester | 208458-89-3

• 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: Phosphorous acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,6-dichloro-phenyl) ester
• CAS: 208458-89-3
• 化学式: C₂₈H₃₃Cl₄N₂O₇PSi
• 分子量: 710.45
• InChiKey: CXFJDWQJKSZSDN-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-imidazolyl)-propan-2-ol 、 Phosphorous acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,6-dichloro-phenyl) ester 在 苯基二硫化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-((S)-6-methyl-4-thioxo-6,7-dihydro-5-oxa-1,3a-diaza-4λ⁵-phospha-inden-4-yloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Imidazo-oxazaphosphorines as Precursors to Chiral Phosphite Triesters

  摘要：

  New bicyclic imidazo-oxazaphosphorines underwent a highly diastereoselective displacement of the imidazole moiety upon reaction with various alcohols, leading to chiral phosphite triesters as single diastereomers. The introduction of a nucleoside on this bicyclic structure was investigated by several routes, leading to new nucleoside building blocks.

  DOI：

  10.1080/07328319808003465
• 作为产物：
  描述：

  5’-O-(叔丁基二甲基甲硅烷基)胸苷 、 Tris(2,6-dichlorophenyl) phosphite 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到Phosphorous acid (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester bis-(2,6-dichloro-phenyl) ester
  参考文献：
  名称：

  Imidazo-oxazaphosphorines as Precursors to Chiral Phosphite Triesters

  摘要：

  New bicyclic imidazo-oxazaphosphorines underwent a highly diastereoselective displacement of the imidazole moiety upon reaction with various alcohols, leading to chiral phosphite triesters as single diastereomers. The introduction of a nucleoside on this bicyclic structure was investigated by several routes, leading to new nucleoside building blocks.

  DOI：

  10.1080/07328319808003465