3',5'-di-O-toluoyl-4'-thiothymidine | 134111-28-7

• 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: 3',5'-di-O-toluoyl-4'-thiothymidine
• 英文别名: [(2R,3S,5R)-3-(4-methylbenzoyl)oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl 4-methylbenzoate
• CAS: 134111-28-7
• 化学式: C₂₆H₂₆N₂O₆S
• 分子量: 494.568
• InChiKey: OPQYLWFZAMXIAT-BHDDXSALSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107.46
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-toluoyl-4'-thiothymidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以78%的产率得到1-[(2R,4S,5R)-4-羟基-5-(羟基甲基)四氢噻吩-2-基]-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides

  摘要：

  2'-Deoxy-4'-thiocytidine (7-beta), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro. All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also active against herpes simplex 1 and human cytomegalovirus in cell culture.

  DOI：

  10.1021/jm00112a007
• 作为产物：
  描述：

  1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose 、 胸腺嘧啶 在 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 生成 3',5'-di-O-toluoyl-4'-thiothymidine 、 1-(2-deoxy-4-thio-3,5-di-O-toluoyl-α-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides

  摘要：

  2'-Deoxy-4'-thiocytidine (7-beta), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro. All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also active against herpes simplex 1 and human cytomegalovirus in cell culture.

  DOI：

  10.1021/jm00112a007