((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol | 268737-87-7

• 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: ((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol
• 英文别名: ((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-enyl)methanol；[(1S,4R)-4-(2,6-dichloropurin-9-yl)cyclopent-2-en-1-yl]methanol
• CAS: 268737-87-7
• 化学式: C₁₁H₁₀Cl₂N₄O
• 分子量: 285.133
• InChiKey: PEAFSPFEGVGMQD-RQJHMYQMSA-N

物化性质

• 沸点：
  414.6±55.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol 在 tin(II) chloride dihydrate 、 一水合肼 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 阿巴卡韦
  参考文献：
  名称：

  对映选择性合成碳环核苷（-）-阿巴卡韦†

  摘要：

  对映体纯的β-内酰胺，在氮上具有适当的吸电子基团，参与了与2，6-二氯嘌呤四丁基铵盐的π-烯丙基钯介导的反应，从而提供了具有高区域选择性和立体选择性的高级顺式-1,4-取代的环戊烯。该高级中间体已成功地被操纵为（-）-Abacavir的总合成物。

  DOI：

  10.1039/c2ob06775g
• 作为产物：
  描述：

  [(1s,Cis)-4-氨基-2-环戊烯-1-甲醇] 在 三甲基氯硅烷 、 亚硝酸正戊酯 、 二正丁基氧化锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 、 正丁醇 为溶剂， 反应 49.0h， 生成 ((1S,4R)-4-(2,6-dichloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol
  参考文献：
  名称：

  [EN] MODIFIED NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS FOR CORONA AND OTHER VIRUSES
  [FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES MODIFIÉS UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX CONTRE LE CORONAVIRUS ET D'AUTRES VIRUS

  摘要：

  Compounds, compositions and methods for preventing, treating or curing a coronavirus infection in human subjects or other animal hosts. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV-2. In another embodiment, the methods are used to treat a patient infected with a Flavivirus, Picornavus, Togavirus, or Bunyavirus.

  公开号：

  WO2022217154A2

文献信息

• Solid-Phase Synthesis of Carbocyclic Nucleosides
  作者：Michael T. Crimmins、William J. Zuercher

  DOI：10.1021/ol005614n

  日期：2000.4.1

  [formula: see text] An efficient solid-phase synthesis of carbocyclic nucleosides has been developed. The key step is the palladium-catalyzed coupling of a purine derivative to a resin-bound allylic benzoate. The resulting products may be further functionalized on the solid phase. Acidic cleavage affords carbocyclic nucleosides, a class of compounds with demonstrated biological activity and substantial

  [化学式：见正文]已经开发了一种有效的固相合成碳环核苷的方法。关键步骤是嘌呤衍生物与树脂结合的烯丙基苯甲酸酯的钯催化偶联。所得产物可以在固相上进一步官能化。酸性裂解提供了碳环核苷，这是一类具有证明的生物活性和当前广泛关注的化合物。
• [EN] PREPARATION OF SYNTHETIC NUCLEOSIDES VIA p-ALLYL TRANSITION METAL COMPLEX FORMATION<br/>[FR] PRÉPARATION DE NUCLÉOSIDES DE SYNTHÈSE AU MOYEN DE LA FORMATION DE COMPLEXES MÉTALLIQUES DE TRANSITION ?-ALLYLIQUES
  申请人：UNIV EMORY

  公开号：WO2009021114A1

  公开（公告）日：2009-02-12

  This invention provides highly regioselective and stereoselective processes for preparing synthetic nucleosides. A process for the preparation of synthetic nucleosides is provided that comprises a) preparing a bicycloamide derivative, b) reacting the bicycloamide derivative with a nucleic acid base or heterocyclic base or salt thereof in the presence of a transition metal catalyst to form a cyclopentenecarboxamide, and c) cleaving a carboxamide group from the cyclopentenecarboxamide to form the synthetic nucleoside. The processes according to the invention can be used for the synthesis of a variety of anti-viral agents, including Abacavir, Carbovir, and Entecavir, as well as derivatives thereof.

  这项发明提供了用于制备合成核苷的高度区域选择性和立体选择性的过程。提供了一种用于制备合成核苷的过程，包括a)制备双环酰胺衍生物，b)将双环酰胺衍生物与核酸碱基或杂环碱基或其盐在过渡金属催化剂存在下反应，形成环戊烯羧酰胺，c)从环戊烯羧酰胺中裂解羧酰胺基团以形成合成核苷。根据该发明的过程可用于合成各种抗病毒药物，包括阿巴卡韦、卡波韦和恩替卡韦，以及其衍生物。
• Preparation Of Synthetic Nucleosides via Pi-Allyl Transition Metal Complex Formation
  申请人：Liotta Dennis C.

  公开号：US20100204463A1

  公开（公告）日：2010-08-12

  This invention provides highly regioselective and stereoselective processes for preparing synthetic nucleosides. A process for the preparation of synthetic nucleosides is provided that comprises a) preparing a bicycloamide derivative, b) reacting the bicycloamide derivative with a nucleic acid base or heterocyclic base or salt thereof in the presence of a transition metal catalyst to form a cyclopentenecarboxamide, and c) cleaving a carboxamide group from the cyclopentenecarboxamide to form the synthetic nucleoside. The processes according to the invention can be used for the synthesis of a variety of anti-viral agents, including Abacavir, Carbovir, and Entecavir, as well as derivatives thereof.