4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazin-3-one | 114184-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazin-3-one
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(3-oxo-1,4-thiazin-4-yl)oxolan-2-yl]methyl benzoate
• CAS: 114184-50-8
• 化学式: C₃₀H₂₅NO₈S
• 分子量: 559.596
• InChiKey: NCBZZBIRMKXSEN-MIRJVGOZSA-N

物化性质

• 沸点：
  731.1±60.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazin-3-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以75%的产率得到4-β-D-ribofuranosyl-1,4-thiazin-3-one
  参考文献：
  名称：

  Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism

  摘要：

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.

  DOI：

  10.1021/jm00403a015
• 作为产物：
  描述：

  2,3,5-三苯甲酰基-beta-D-呋喃核糖 、 3-<(trimethylsilyl)oxy>-1,4-thiazine 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以78%的产率得到4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazin-3-one
  参考文献：
  名称：

  Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism

  摘要：

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.

  DOI：

  10.1021/jm00403a015