5-(2-thienyl)-6-aza-β-2'-deoxyuridine | 156270-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5-(2-thienyl)-6-aza-β-2'-deoxyuridine
• 英文别名: 2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6-(2-thienyl)-1,2,4-triazine-3,5-dione；2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-thiophen-2-yl-1,2,4-triazine-3,5-dione
• CAS: 156270-75-6
• 化学式: C₁₂H₁₃N₃O₅S
• 分子量: 311.318
• InChiKey: GMYPYFRQOLNVPY-LKEWCRSYSA-N

物化性质

• 密度：
  1.82±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(2-thienyl)-6-aza-β-2'-deoxyuridine 在 吡啶 、 溴 作用下， 以 四氯化碳 、 氯仿 为溶剂， 反应 1.75h， 生成 5-<2-(5-bromothienyl)>-1-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)-6-azauracil
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233
• 作为产物：
  描述：

  2-噻吩乙醛酸 在 sodium hydroxide 、 sodium methylate 、 氯乙酸 、 六甲基二硅氮烷 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 62.0h， 生成 5-(2-thienyl)-6-aza-β-2'-deoxyuridine
  参考文献：
  名称：

  The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines

  摘要：

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

  DOI：

  10.1080/15257779408013233

文献信息

• The Synthesis of Some 5-Substituted-6-aza-2′-deoxyuridines
  作者：I. Basnak、P. L. Coe、R. T. Walker

  DOI：10.1080/15257779408013233

  日期：1994.3

  5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-beta-D-erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as beta anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br-2/CCl4 and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].