3-Carbamoyl-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-pyridinium; bromide | 133473-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-Carbamoyl-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-pyridinium; bromide
• CAS: 133473-74-2
• 化学式: Br*C₁₁H₁₄FN₂O₄
• 分子量: 337.146
• InChiKey: KJGKIQJGWBRAMA-ADJAGLGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.33
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  96.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Carbamoyl-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-pyridinium; bromide 在 焦磷酰氯 作用下， 以 various solvent(s) 为溶剂， 反应 18.0h， 生成 ((2R,3R,4S,5S)-5-(3-carbamoylpyridin-1-ium-1-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methyl hydrogen phosphate 、 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)nicotinamide-5'-phosphate
  参考文献：
  名称：

  Pyridine coenzyme analogs. 3. Synthesis of three NAD+ analogs containing a 2'-deoxy-2'-substituted nicotinamide arabinofuranosyl moiety

  摘要：

  A general method for the preparation of 2'-deoxy-2'-substituted arabino-nicotinamide-adenine dinucleotide (NAD) analogues is described. Starting from 1,2:5,6-di-O-isopropylidine-alpha-D-allofuranose, the 2'-amino-, 2'-azido-, and 2'-fluoro-arabino-NAD analogues have been prepared. We report an improved phosphorylation procedure for nicotinamide nucleosides using pyrophosphoryl chloride in m-cresol. The selective reduction of azido substituents by aqueous dithiothreitol (DTT) in the presence of the readily reducible nicotinamide moiety is also reported. With both the 2'-azido and the 2'-fluoro substituents the cis configuration predominates for the incoming nicotinamide, thus allowing the stereoselective formation of the beta anomer in high yield.

  DOI：

  10.1021/jo00011a029
• 作为产物：
  描述：

  2-fluoro-2-deoxy-5-O-(p-nitrobenzoyl)-D-arabinofuranose 在 吡啶 、 氨 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-Carbamoyl-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-pyridinium; bromide
  参考文献：
  名称：

  Pyridine coenzyme analogs. 3. Synthesis of three NAD+ analogs containing a 2'-deoxy-2'-substituted nicotinamide arabinofuranosyl moiety

  摘要：

  A general method for the preparation of 2'-deoxy-2'-substituted arabino-nicotinamide-adenine dinucleotide (NAD) analogues is described. Starting from 1,2:5,6-di-O-isopropylidine-alpha-D-allofuranose, the 2'-amino-, 2'-azido-, and 2'-fluoro-arabino-NAD analogues have been prepared. We report an improved phosphorylation procedure for nicotinamide nucleosides using pyrophosphoryl chloride in m-cresol. The selective reduction of azido substituents by aqueous dithiothreitol (DTT) in the presence of the readily reducible nicotinamide moiety is also reported. With both the 2'-azido and the 2'-fluoro substituents the cis configuration predominates for the incoming nicotinamide, thus allowing the stereoselective formation of the beta anomer in high yield.

  DOI：

  10.1021/jo00011a029