1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine | 644961-34-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine
• 英文别名: [(2R,3R,4R,5R)-4-benzoyloxy-5-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-2-[(2-phenoxyacetyl)oxymethyl]oxolan-3-yl] benzoate
• CAS: 644961-34-2
• 化学式: C₃₇H₃₆N₂O₁₃
• 分子量: 716.698
• InChiKey: XGCAHOZXGNOUIY-RRWPIJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  190.91
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine 在 吡啶 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 16.67h， 生成 1-[5-O-(4'-monomethoxytrityl)-3-O-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Synthesis and Properties of Phosphorylated 3′-O-β-D-Ribofuranosyl-2′-deoxythymidine

  摘要：

  A strategy was developed for the synthesis of 3'-O-beta-D-ribofuranosyl 2'-deoxythymidine derivatives using three different protecting groups, which allows the synthesis of a phosphoramidite building block for oligonucleotide synthesis. Likewise the 5'-O- and 5"-O-phosphorylated analogues were synthesized and their conformation was determined using NMR spectroscopy.

  DOI：

  10.1081/ncn-120022028
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.83h， 生成 1-[3-O-(2,3-di-O-benzoyl-5-O-phenoxyacetyl-β-D-ribofuranosyl)-2-deoxy-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Synthesis and Properties of Phosphorylated 3′-O-β-D-Ribofuranosyl-2′-deoxythymidine

  摘要：

  A strategy was developed for the synthesis of 3'-O-beta-D-ribofuranosyl 2'-deoxythymidine derivatives using three different protecting groups, which allows the synthesis of a phosphoramidite building block for oligonucleotide synthesis. Likewise the 5'-O- and 5"-O-phosphorylated analogues were synthesized and their conformation was determined using NMR spectroscopy.

  DOI：

  10.1081/ncn-120022028