Phosphoric acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester hexadecyl ester (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester | 259185-59-6

• 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: Phosphoric acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester hexadecyl ester (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
• CAS: 259185-59-6
• 化学式: C₅₄H₇₇N₂O₁₅P
• 分子量: 1025.18
• InChiKey: MAEHRNNEKXAYLV-DQTJULLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.62
• 重原子数：
  72.0
• 可旋转键数：
  31.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  215.69
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester hexadecyl ester (2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 在 三氯乙酸 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以100%的产率得到1-[(2R,4S,5R)-5-[[hexadecoxy-oxido-[[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]phosphaniumyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  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：

  3’-O-(4,4’-二甲氧基三苯甲基)胸苷 在 1H-1,2,4-三唑 、 N-甲基咪唑 、 sodium hydroxide 、 MSNT 、 三苯基氯硅烷 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 为溶剂， 反应 3.67h， 生成 Phosphoric acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl 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