4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazine-2,3-dione | 114184-52-0

• 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-thiazine-2,3-dione
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2,3-dioxo-1,4-thiazin-4-yl)oxolan-2-yl]methyl benzoate
• CAS: 114184-52-0
• 化学式: C₃₀H₂₃NO₉S
• 分子量: 573.58
• InChiKey: PSKIBOAPYJFAAD-PMHJDTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazine-2,3-dione 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以55%的产率得到4-β-D-ribofuranosyl-1,4-thiazine-2,3-dione
  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：

  4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazin-3-one 在 间氯过氧苯甲酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以16%的产率得到4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,4-thiazine-3-one 1-oxide
  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