(S-β-D-glucopyranosidyl-2-thioethyl) [S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate | 195535-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S-β-D-glucopyranosidyl-2-thioethyl) [S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]sulfanylethoxy]phosphoryl]oxyethylsulfanyl]tetrahydropyran-2-yl]methyl acetate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylethoxy]phosphoryl]oxyethylsulfanyl]oxan-2-yl]methyl acetate
• CAS: 195535-40-1
• 化学式: C₃₄H₅₀N₅O₂₁PS₂
• 分子量: 959.898
• InChiKey: GJEHPHJUSLUFIJ-VZXKDYGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  63
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  373
• 氢给体数：
  5
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  (S-β-D-glucopyranosidyl-2-thioethyl) [S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate 以 水 为溶剂， 反应 8.8h， 生成 (S-β-D-glucopyranosidyl-2-thioethyl) 3'-azido-3'-deoxythymidin-5'-yl phosphate sodium salt 、 [S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate sodium salt
  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
• 作为产物：
  描述：

  2-bromoethyl 1-deoxy-1-thio-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 Dowex 50WX2 <(n-C4H9)N⁺ form> 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 14.0h， 生成 (S-β-D-glucopyranosidyl-2-thioethyl) [S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosidyl)-2-thioethyl] 3'-azido-3'-deoxythymidin-5'-yl phosphate
  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