Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphoryloxy]-ethylsulfanyl}-tetrahydro-pyran-4-yl ester | 195535-43-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphoryloxy]-ethylsulfanyl}-tetrahydro-pyran-4-yl ester
• CAS: 195535-43-4
• 化学式: C₂₉H₃₉N₆O₁₆PS
• 分子量: 790.699
• InChiKey: AGONDBJDTPDUND-CKERXDCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  295.83
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphoryloxy]-ethylsulfanyl}-tetrahydro-pyran-4-yl ester 在 Dowex 50WX₂ (Na⁺ form) 、 Dowex 50WX2 <(n-C4H9)N⁺ form> 、 sodium methylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 12.67h， 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
• 作为产物：
  描述：

  (2-hydroxy)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 四氮唑 、 叔丁基过氧化氢 、 二异丙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{2-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-(2-cyano-ethoxy)-phosphoryloxy]-ethylsulfanyl}-tetrahydro-pyran-4-yl 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