[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl bis(2-chlorophenyl) phosphate | 145550-46-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl bis(2-chlorophenyl) phosphate
• CAS: 145550-46-5
• 化学式: C₂₈H₃₅Cl₂N₂O₈PSi
• 分子量: 657.56
• InChiKey: JRVZOZVHMSYMLJ-ISJGIBHGSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  42.0
• 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：
  118.08
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  双(2-氯苯基)磷酰氯 、 3'-O-(叔丁基二甲基硅烷基)胸苷 在 叔丁基锂 作用下， 生成 [(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl bis(2-chlorophenyl) phosphate
  参考文献：
  名称：

  O-selective phosphorylation of nucleosides without N-protection

  摘要：

  A facile chemoselective O-phosphorylation of N-unprotected nucleosides has been achieved via metal alkoxide formation. Sequential treatment of N-unprotected nucleosides with an equimolar amount of a metallo-organic base such as an alkyllithium, potassium tert-butoxide, tert-butylmagnesium chloride, LiAl[N(CH3)2]4, Al[N(CH3)2]3, (i-C4H9)2AlH, etc., and a phosphorochloridate or p-nitrophenyl phosphate results in rapid O-phosphorylation to give the corresponding nucleotides in high yield. The method using magnesium alkoxides is among the best, considering its chemoselectivity, generality, and operational simplicity. The origin of the observed chemoselectivity is discussed.

  DOI：

  10.1021/jo00054a020

文献信息

• Facile nucleoside phoshorylation via hydroxyl activation
  作者：Y. Hayakawa、Y. Aso、M. Uchiyama、R. Noyori

  DOI：10.1016/s0040-4039(00)86393-5

  日期：1983.1