(2R,3R,4S,5R)-6-N-pivaloyl-9--2-furanyl>adenine | 132178-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-6-N-pivaloyl-9--2-furanyl>adenine
• 英文别名: N-[9-[(2R,3R,4S,5R)-5-(dimethoxyphosphorylmethoxy)-3,4-dihydroxyoxolan-2-yl]purin-6-yl]-2,2-dimethylpropanamide
• CAS: 132178-55-3
• 化学式: C₁₇H₂₆N₅O₈P
• 分子量: 459.396
• InChiKey: WFDUKEBFTTXINT-BVIHXZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  167
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R)-6-N-pivaloyl-9--2-furanyl>adenine 生成 (2R,3R,4S,5R)-9-adenine ammonium salt
  参考文献：
  名称：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV

  摘要：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).

  DOI：

  10.1021/jo00008a013
• 作为产物：
  描述：

  2(R)-adenin-9-yl-2,3-dihydrofuran 在 吡啶 、 4-甲基吡啶氧化物 、 4-二甲氨基吡啶 、 四氧化锇 、 一溴化碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 苯硼酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 9.58h， 生成 (2R,3R,4S,5R)-6-N-pivaloyl-9--2-furanyl>adenine
  参考文献：
  名称：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV

  摘要：

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).

  DOI：

  10.1021/jo00008a013

文献信息

• KIM, CHOUNG UN;LUH, BING Y.;MARTIN, JOHN C., J. ORG. CHEM., 56,(1991) N, C. 2642-2647
  作者：KIM, CHOUNG UN、LUH, BING Y.、MARTIN, JOHN C.

  DOI：——

  日期：——
• Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: synthesis of phosphonate nucleotide analogs with potent activity against HIV
  作者：Choung Un Kim、Bing Y. Luh、John C. Martin

  DOI：10.1021/jo00008a013

  日期：1991.4

  Regiospecific and highly stereoselective electrophilic addition to furanoid glycals has been used as a key step in the synthesis of phosphonate isosteres of nucleoside monophosphates. Using this methodology, phosphonate analogues of 1 (ddA), 4 (d4T), and 5 (d4A) monophosphates have been prepared. Present studies have also led to the development of a scheme for the synthesis of the phosphonate isostere of adenosine monophosphate. Despite the acetal structure, phosphonate derivatives 27 and 28 were substantially more acid stable than the corresponding nucleosides 1 and 5 with respect to glycosidic bond cleavage. The phosphonates 22 and 27 exhibited a potent antiretroviral activity comparable to that of 4 (d4T).