[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2,4-dichlorophenyl) hexadecyl phosphate | 259185-51-8

• 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: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2,4-dichlorophenyl) hexadecyl phosphate
• CAS: 259185-51-8
• 化学式: C₅₃H₆₇Cl₂N₂O₁₀P
• 分子量: 994.002
• InChiKey: AYIGOZJNOBHZNZ-VQUQQYROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  68
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2,4-dichlorophenyl) hexadecyl phosphate 在 N-甲基咪唑 、 sodium hydroxide 、 三苯基氯硅烷 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 3.0h， 生成 Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester hexadecyl ester (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Straightforward Synthesis of Lipophilic Thymidine Glucopyranosyl Monophosphates as Models for a Drug Delivery System Across Cellular Membranes

  摘要：

  O-methyl (3'-6) and (5'-6) thymidinyl gluco- and mannopyranosides and (3'-6) thymidinyl glucofuranose can be synthesised in excellent yields by applying the phosphotriester method. The lipophilic phosphotriesters thus obtained are designed as carriers of nucleoside drugs across cellular membranes.

  DOI：

  10.1080/07328319908044627
• 作为产物：
  描述：

  2,4-dichlorophenylphosphorodichloridate 在 1H-1,2,4-三唑 、 N-甲基咪唑 、 MSNT 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 0.67h， 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2,4-dichlorophenyl) hexadecyl phosphate
  参考文献：
  名称：

  Straightforward Synthesis of Lipophilic Thymidine Glucopyranosyl Monophosphates as Models for a Drug Delivery System Across Cellular Membranes

  摘要：

  O-methyl (3'-6) and (5'-6) thymidinyl gluco- and mannopyranosides and (3'-6) thymidinyl glucofuranose can be synthesised in excellent yields by applying the phosphotriester method. The lipophilic phosphotriesters thus obtained are designed as carriers of nucleoside drugs across cellular membranes.

  DOI：

  10.1080/07328319908044627