1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine | 124355-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine
• 英文别名: 1-<5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine
• CAS: 124355-37-9
• 化学式: C₃₁H₂₉N₅O₄
• 分子量: 535.602
• InChiKey: PHNOGHYWHZRJGD-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104.03
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以75%的产率得到1-<3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine
  参考文献：
  名称：

  Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines

  摘要：

  Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.

  DOI：

  10.1021/jm00164a063
• 作为产物：
  描述：

  1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 19.75h， 生成 1-(5-O-trityl-3-(1,2,4-triazol-1-yl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines

  摘要：

  Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.

  DOI：

  10.1021/jm00164a063