methyl 5-carbamoyl-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isothiazole-4-carboxylate | 156270-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-carbamoyl-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isothiazole-4-carboxylate
• CAS: 156270-89-2
• 化学式: C₃₂H₂₆N₂O₁₀S
• 分子量: 630.632
• InChiKey: LLSVEWUGIRAIBQ-ATPOPXNDSA-N

物化性质

• 沸点：
  716.0±60.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  170.41
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 5-carbamoyl-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isothiazole-4-carboxylate 在 盐酸 、 barium dihydroxide 、 Dowex 50W-X₂ (H(+) form) 、 Dowex 50W-X₂(H(+) form) 、 溴 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 13.75h， 生成 3-β-D-ribofuranosyl-isothiazolo<4,5-d>pyrimidine-7(6H)-one
  参考文献：
  名称：

  Synthesis of Novel Isothiazole and Isothiazolo[4,5-d] Pyrimidine Analogues of the NaturalC-Nucleosides Pyrazofurin and the Formycins

  摘要：

  The cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfide with dimethyl acetylenedicarboxylate or with dimethyl fumarate followed by DDQ oxidation was found to give the benzoyl protected dimethyl 3-beta-D-ribofuranosyl-isothiazoledicarboxylate 10. This compound was converted to C-nucleosides 7a, 8 and 9, analogues of pyrazofurin, oxoformycin B and formycin respectively. Despite their structural similarities they did show neither antiviral nor antitumor activity.

  DOI：

  10.1080/15257779408013275
• 作为产物：
  描述：

  dimethyl 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isothiazoline-4,5-dicarboxylate 在 氨 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 氯仿 、 氯苯 为溶剂， 反应 6.5h， 生成 methyl 5-carbamoyl-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-isothiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of Novel Isothiazole and Isothiazolo[4,5-d] Pyrimidine Analogues of the NaturalC-Nucleosides Pyrazofurin and the Formycins

  摘要：

  The cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfide with dimethyl acetylenedicarboxylate or with dimethyl fumarate followed by DDQ oxidation was found to give the benzoyl protected dimethyl 3-beta-D-ribofuranosyl-isothiazoledicarboxylate 10. This compound was converted to C-nucleosides 7a, 8 and 9, analogues of pyrazofurin, oxoformycin B and formycin respectively. Despite their structural similarities they did show neither antiviral nor antitumor activity.

  DOI：

  10.1080/15257779408013275