adenosine 6-N- | 154534-47-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: adenosine 6-N-
• 英文别名: 6-N-(diethylphosphoryl)adenosine；(2R,3R,4S,5R)-2-[6-(diethoxyphosphorylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 154534-47-1
• 化学式: C₁₄H₂₂N₅O₇P
• 分子量: 403.332
• InChiKey: NHIWFEZJNKEPKW-IDTAVKCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  腺苷 在 吡啶 、 四氮唑 、 叔丁基过氧化氢 、 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 2.67h， 生成 adenosine 6-N-
  参考文献：
  名称：

  Synthesis and Properties of N-Phosphorylated Ribonucleosides

  摘要：

  A new class of phosphorylated nucleosides, i.e., adenosine 6-N-phosphoramidate (6-N-AMP) and related derivatives, were synthesized in good yields via phosphitylation of the amino group of appropriately protected adenosine derivatives. In a similar manner, cytidine 4-N-phosphoramidate (4-N-CMP), guanosine 2-N-phosphoramidate (2-N-GMP), and their diethyl ester derivatives were synthesized. These new compounds were characterized by H-1, C-13, and P-31 NMR, UV, CD, IR, electrophoresis, and mass spectroscopy. The physical and chemical properties of these N-phosphorylated ribonucleoside derivatives have been studied in detail.

  DOI：

  10.1021/ja00101a011

文献信息

• Nucleic acid related compounds.<b>81</b>. Syntheses of 9-(3-deoxy-β-D-<i>threo</i>-pentofuranosyl)adenine, the core nucleoside of the extraordinarily selective antibiotic agrocin 84, and simplified structural component analogues
  作者：Ravi Vinayak、Fritz Hansske、Morris J. Robins

  DOI：10.1002/jhet.5570300504

  日期：1993.10

  Alternative syntheses of 9-(3-deoxy-β-D-threo-pentofuranosyl)adenine (4), the core nucleoside of agrocin 84 [and its 2′-deoxy threo isomer 5] were devised: (1) direct conversion of 9-(β-D-arabinofuranosyl)adenine into 9-(2,3-anhydro-β-D-lyxofuranosyl)adenine and regioselective opening of its oxirane ring with sodium borohy-dride to give 4 and 5(˜7.5:1); (2) treatment of adenosine with sodium hydride

  设计了9-（3-脱氧-β-D-苏-戊呋喃糖基）腺嘌呤的替代合成方法（4），农杆菌素84 [及其2'-脱氧苏式异构体5 ]的核心核苷：（1）直接转化9 -将（-β-D-阿拉伯呋喃糖基）腺嘌呤转化成9-（2,3-脱水-β-D-呋喃糖基）腺嘌呤，并用硼氢化钠将其环氧乙烷环区域选择性地打开，得到4和5（〜7.5：1）；（2）用氢化钠和2,4,6-三异丙基苯-磺酰氯处理腺苷，并用三乙基硼氢化锂将所得的2'（3'）-磺酸盐进行还原性[1,2]-氢化物移位重排，得到三乙基硼氢化锂。给4和5（〜2：1）; （3）对9- [2（3），5-双-O-（叔丁基二甲基甲硅烷基）-β-D-阿拉伯呋喃糖基]腺嘌呤的苯氧基硫代羰基酯进行巴顿脱氧，并脱保护得到4和2 ′-脱氧腺苷（〜5∶1）。方法（2）和（3）给出的产率较低。探索了简化的6- N-和5'- O-腺苷氨基磷酸酯模型化合物的合成，以检查针对农杆菌素84提出的结构中此类特征的潜在途径。