1-((2S,3S,4S,5R)-3-Amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-carbamoyl-pyridinium; chloride | 133473-59-3

• 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: 1-((2S,3S,4S,5R)-3-Amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-carbamoyl-pyridinium; chloride
• 英文别名: 1-[(2S,3S,4S,5R)-3-amino-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboxamide;chloride
• CAS: 133473-59-3
• 化学式: C₁₁H₁₆N₃O₄*Cl
• 分子量: 289.719
• InChiKey: SBDOJDDQNSPJNG-ADJAGLGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.35
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-((2R,3S,4S,5R)-3-Azido-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-carbamoyl-pyridinium; chloride 、 1-((2S,3S,4S,5R)-3-Azido-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-carbamoyl-pyridinium; chloride 生成 1-((2S,3S,4S,5R)-3-Amino-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-carbamoyl-pyridinium; chloride
  参考文献：
  名称：

  SLEATH, PAUL R.;HANDLON, ANTHONY L.;OPPENHEIMER, NORMAN J., J. ORG. CHEM., 56,(1991) N1, C. 3608-3613

  摘要：

  DOI：

文献信息

• Pyridine coenzyme analogs. 3. Synthesis of three NAD+ analogs containing a 2'-deoxy-2'-substituted nicotinamide arabinofuranosyl moiety
  作者：Paul R. Sleath、Anthony L. Handlon、Norman J. Oppenheimer

  DOI：10.1021/jo00011a029

  日期：1991.5

  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.