Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester bis-[2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl] ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester bis-[2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl] ester
• 英文别名: Bis-(glucopyranosylthio)-ethyl phosphotriester derative of AZT；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl bis[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethyl] phosphate
• 化学式: C₂₆H₄₂N₅O₁₇PS₂
• 分子量: 791.749
• InChiKey: PDCBOFJEZYIGRG-DNWJZDBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  349
• 氢给体数：
  9
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  bis[S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate 在 Dowex resin (OH^-) 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以68%的产率得到Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester bis-[2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl] ester
  参考文献：
  名称：

  Synthesis and Studies of Mononucleoside Glucosyl Phosphotriester Derivatives

  摘要：

  The synthesis and stability studies in several aqueous media of mononucleoside glucosyl phosphotriester derivatives of 3'-azido-3'-deoxythymidine are reported herein, Such neutral mononucleotides, which incorporate beta-glucopyranosidyl moieties associated to a thioethyl Linker as phosphate protecting groups were designed to act as ''pronucleotides'', giving rise to the corresponding 5'-mononucleotide through a glucosidase-mediated activation mechanism.

  DOI：

  10.1021/jo9706638