N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-4-methylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-4-methylbenzenesulfonamide
• 英文别名: 5-amino-5'-adenosine p-toluenesulfonate
• 化学式: C₁₇H₂₀N₆O₅S
• 分子量: 420.449
• InChiKey: ZTGLCSYSEGGUFP-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  174
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ferrocenoyl hydroxybenzotriazole ester 、 N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-4-methylbenzenesulfonamide 以 四氢呋喃 为溶剂， 以80%的产率得到5-ferroceneamido-5'-adenosine
  参考文献：
  名称：

  Synthesis and electrochemistry of 5-ferrocene-glucosamide, 5-ferrocene-glucosamide phosphate and 5-ferrocene-amido-5-adenosine in aqueous solution

  摘要：

  The syntheses of new ferrocene-monosaccharide compounds, 5-ferrocene-glucosamide (4), 5-ferrocene-glucosamido-2'-phosphate (5), and 5'-ferrocene-amido-5'-deoxyadenosine (6), are reported starting from ferrocenoyl hydroxybenzotriazole ester and the corresponding amino sugars. All compounds are investigated spectroscopically. In addition, their redox properties are investigated by cyclic voltarnmetry in aqueous solution. These compounds show a reversible one-electron oxidation. This redox potential in the case of 4 exhibits a significant pH dependence. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01414-0
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 甲酸 、 偶氮二甲酸二异丙酯 、 水 、 caesium carbonate 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Parallel Solution-Phase Synthesis of an Adenosine Antibiotic Analog Library

  摘要：

  A library of eighty one adenosine antibiotic analogs was prepared under the Pilot Scale Library Program of the NIH Roadmap initiative from 5'-amino-5'-deoxy-2',3'-O-isopropylidene-adenosine 3. Diverse aldehyde, sulfonyl chloride and carboxylic acid reactant sets were condensed to 3, in solution-phase fashion, leading after acid-mediated hydrolysis to the targeted compounds in good yields and high purity. No marked antituberculosis or anticancer activity was noted on preliminary cellular testing, but these nucleoside analogs should be useful candidates for other types of biological activity.

  DOI：

  10.1021/co300127z