(+)-2-amino-9-((1R,4S)-4-(2-hydroxyethyl)cyclopent-2-enyl)-9H-purin-6-ol | 1269440-02-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+)-2-amino-9-((1R,4S)-4-(2-hydroxyethyl)cyclopent-2-enyl)-9H-purin-6-ol
• 英文别名: 2-amino-9-[(1R,4S)-4-(2-hydroxyethyl)cyclopent-2-en-1-yl]-1H-purin-6-one
• CAS: 1269440-02-9
• 化学式: C₁₂H₁₅N₅O₂
• 分子量: 261.283
• InChiKey: WZPBGVWIYFVQSF-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,4R)-乙酸-4-叔丁氧羰基氨基-环戊基-2-烯酯 在 盐酸 、 甲醇 、 偶氮二甲酸二异丙酯 、 水 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 、 1,2-双(二苯基膦)乙烷 、 sodium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 、 异丙醇 、 正丁醇 为溶剂， 反应 131.17h， 生成 (+)-2-amino-9-((1R,4S)-4-(2-hydroxyethyl)cyclopent-2-enyl)-9H-purin-6-ol
  参考文献：
  名称：

  Enantioselective syntheses of carbocyclic nucleosides 5′-homocarbovir, epi-4′-homocarbovir, and their cyclopropylamine analogs using facially selective Pd-mediated allylations

  摘要：

  Carbocyclic nucleosides (-)-5'-homocarbovir and (+)-epi-4'-homocarbovir were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylative allylations of allyl 2,2,2-trifluoroethyl malonates were used to install the 4'-hydroxyethyl groups. Late stage derivatization gave access to the cyclopropylamine analogs, (-)-5'-homoabacavir, and (+)-epi-4'-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.097

文献信息

• Enantioselective syntheses of carbocyclic nucleosides 5′-homocarbovir, epi-4′-homocarbovir, and their cyclopropylamine analogs using facially selective Pd-mediated allylations
  作者：Lawrence P. Tardibono、Marvin J. Miller、Jan Balzarini

  DOI：10.1016/j.tet.2010.11.097

  日期：2011.2

  Carbocyclic nucleosides (-)-5'-homocarbovir and (+)-epi-4'-homocarbovir were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylative allylations of allyl 2,2,2-trifluoroethyl malonates were used to install the 4'-hydroxyethyl groups. Late stage derivatization gave access to the cyclopropylamine analogs, (-)-5'-homoabacavir, and (+)-epi-4'-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity. (C) 2010 Elsevier Ltd. All rights reserved.