1-O-acetyl-5-azido-2,3-di-O-benzoyl-5-deoxy-β-D-ribofuranoside | 174019-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-5-azido-2,3-di-O-benzoyl-5-deoxy-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5S)-5-acetyloxy-2-(azidomethyl)-4-benzoyloxyoxolan-3-yl] benzoate
• CAS: 174019-82-0
• 化学式: C₂₁H₁₉N₃O₇
• 分子量: 425.398
• InChiKey: RZOQUSKDNLFHLZ-NEYJZJCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-5-azido-2,3-di-O-benzoyl-5-deoxy-β-D-ribofuranoside 在 palladium on activated charcoal 吡啶 、 三甲基氯硅烷 、 TMSTf 、 氢气 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 为溶剂， 反应 64.0h， 生成 [(2R,3R,4R,5R)-5-(4-amino-5-cyanopyrrolo[2,3-d]pyrimidin-7-yl)-4-benzoyloxy-2-[[(4-nitrophenyl)sulfonylamino]methyl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives

  摘要：

  A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azidod-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

  DOI：

  10.1080/15257779508010707
• 作为产物：
  描述：

  methyl 5-deoxy-5-azido-β-D-ribofuranozide 在 吡啶 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 23.0h， 生成 1-O-acetyl-5-azido-2,3-di-O-benzoyl-5-deoxy-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives

  摘要：

  A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azidod-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

  DOI：

  10.1080/15257779508010707