cpAP | 162119-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: cpAP
• 英文别名: (+/-)-9-(4-β-Phosphonomethoxycyclopent-2-en-1-β-yl)adenine；[(1S,4R)-4-(6-aminopurin-9-yl)cyclopent-2-en-1-yl]oxymethylphosphonic acid
• CAS: 162119-15-5
• 化学式: C₁₁H₁₄N₅O₄P
• 分子量: 311.237
• InChiKey: XZODRISOVMXWBO-JGVFFNPUSA-N

物化性质

• 沸点：
  673.3±65.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cpAP 在 三丁基焦磷酸铵 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1'R,4'S)-9-<4'-(diphosphorylphosphonomethoxy)cyclopent-2'-enyl>adenine
  参考文献：
  名称：

  Synthesis of Four Stereoisomers of Carbocyclic 5'-NOR D4A and Evaluation of Their Triphosphates as Substrates for DNA Polymerases

  摘要：

  A method was developed for synthesis of the four stereoisomeric enantiomerically pure 5'-nor carbocyclic nucleosides 4b, ent-4b, 10 and ent-10 starting from the common enantiomerically pure allylic monoacetate 1. Nucleoside analogues were converted to the corresponding triphosphate derivatives 6, ent-6, 12, and ent-12. The substrate properties of the latters towards different DNA polymerases were evaluated.

  DOI：

  10.1080/15257779508012458
• 作为产物：
  描述：

  (1S,4R)-4-(6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ol 在 三甲基溴硅烷 、 氨 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 cpAP
  参考文献：
  名称：

  立体合成碳环2'，3'-二脱氧-2'，3'-二氢-5'-芥子苷的四个立体异构体二膦酰基膦酸酯

  摘要：

  已经开发了从常见的对映体纯的烯丙基单乙酸酯3开始的四个立体异构对映体纯的5'-去碳环腺苷类似物4b，ent - 4b，5b和ent - 5b的灵活合成。将每个核苷类似物分别转化为相应的4'-膦酸酯，然后分别转化为二磷酸基膦酸酯4e，ent - 4e，5e和ent - 5e。

  DOI：

  10.1016/0040-4020(94)00986-5

文献信息

• Carbocyclic nucleosides and nucleotides
  申请人：INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE ACADEMY OF SCIENCES OF THE CZECH REPUBLIC

  公开号：EP0369409B1

  公开（公告）日：1995-01-04
• US5744600A
  申请人：——

  公开号：US5744600A

  公开（公告）日：1998-04-28
• Stereocontrolled synthesis of the four stereoisomeric diphosphorylphosphonates of carbocyclic 2′,3′-dideoxy-2′,3′-didehydro-5′-noradenosine
  作者：Natalia B. Dyatkina、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1016/0040-4020(94)00986-5

  日期：1995.1

  A flexible synthesis of the four stereoisomeric enantiomerically pure 5′-nor carbocyclic adenosine analogues 4b, ent-4b, 5b and ent-5b starting from the common enantio-merically pure allylic monoacetate 3 has been developed. Each of the nucleoside analogues was transformed into the corresponding 4′-phosphonates and subsequently into the diphosphoryl-phosphonates 4e, ent-4e, 5e, and ent-5e, respectively

  已经开发了从常见的对映体纯的烯丙基单乙酸酯3开始的四个立体异构对映体纯的5'-去碳环腺苷类似物4b，ent - 4b，5b和ent - 5b的灵活合成。将每个核苷类似物分别转化为相应的4'-膦酸酯，然后分别转化为二磷酸基膦酸酯4e，ent - 4e，5e和ent - 5e。
• Synthesis of Four Stereoisomers of Carbocyclic 5'-NOR D4A and Evaluation of Their Triphosphates as Substrates for DNA Polymerases
  作者：Natalia Dyatkina、Dniitry Semizarov、Lyubov Victorova、Alexander Krayevsky、Fritz Theil、Martin von Janta-Lipinski

  DOI：10.1080/15257779508012458

  日期：1995.5.1

  A method was developed for synthesis of the four stereoisomeric enantiomerically pure 5'-nor carbocyclic nucleosides 4b, ent-4b, 10 and ent-10 starting from the common enantiomerically pure allylic monoacetate 1. Nucleoside analogues were converted to the corresponding triphosphate derivatives 6, ent-6, 12, and ent-12. The substrate properties of the latters towards different DNA polymerases were evaluated.