(S)-1-(6-chloro-9H-purin-9-yl) propan-2-ol | 743358-22-7

• 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: (S)-1-(6-chloro-9H-purin-9-yl) propan-2-ol
• 英文别名: (2S)-1-(6-chloropurin-9-yl)propan-2-ol
• CAS: 743358-22-7
• 化学式: C₈H₉ClN₄O
• 分子量: 212.639
• InChiKey: LVNBNKMMTVWRJO-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  三甲基氯硅烷 、 (S)-1-(6-chloro-9H-purin-9-yl) propan-2-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-6-chloro-9-(2-((trimethylsilyl)oxy)propyl)-9H-purine
  参考文献：
  名称：

  The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation

  摘要：

  A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.

  DOI：

  10.1021/ol500583d
• 作为产物：
  描述：

  1-(6-氯-9H-嘌呤-9-基)-2-丙酮 在 [RuCl2(benzene)]2 、 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 sodium formate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以97%的产率得到(S)-1-(6-chloro-9H-purin-9-yl) propan-2-ol
  参考文献：
  名称：

  The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation

  摘要：

  A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.

  DOI：

  10.1021/ol500583d

文献信息

• Chemoenzymatic Synthesis of Tenofovir
  作者：Beata Zdun、Tamara Reiter、Wolfgang Kroutil、Paweł Borowiecki

  DOI：10.1021/acs.joc.3c01005

  日期：2023.8.4

  routes toward tenofovir using low-cost starting materials and commercial or homemade enzyme preparations as biocatalysts. The biocatalytic key step was accomplished either via stereoselective reduction using an alcohol dehydrogenase or via kinetic resolution using a lipase. By employing a suspension of immobilized lipase from Burkholderia cepacia (Amano PS-IM) in a mixture of vinyl acetate and toluene, the

  我们报告了使用低成本起始材料和商业或自制酶制剂作为生物催化剂的替诺福韦的新化学酶途径。生物催化关键步骤是通过使用醇脱氢酶的立体选择性还原或通过使用脂肪酶的动力学拆分来完成的。通过使用来自洋葱伯克霍尔德氏菌(Amano PS-IM)的固定化脂肪酶在乙酸乙烯酯和甲苯混合物中的悬浮液，在 47 小时内获得了 500 mg 规模 (60 mM)所需的 ( R )-酯 (99% ee)。 ％ 屈服。或者，由含有开菲尔乳杆菌重组乙醇脱氢酶 (ADH) 的冻干大肠杆菌细胞催化立体选择性还原 1-(6-氯-9 H-嘌呤-9-基) 丙-2-酮 (84 mg，100 mM) ( E. coli /Lk-ADH Prince) 使相应的 ( R )-醇达到定量转化、86% 产率和优异的光学纯度 (>99% ee)。关键的( R )-中间体通过“一锅法”氨解——( R )-乙酸酯在NH 3 -饱和甲醇中水解，所得(
• The Synthesis of Tenofovir and Its Analogues via Asymmetric Transfer Hydrogenation
  作者：Qian Zhang、Bai-Wei Ma、Qian-Qian Wang、Xing-Xing Wang、Xia Hu、Ming-Sheng Xie、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol500583d

  日期：2014.4.4

  A series of tenofovir analogues with potential antiviral and immunobiologically active compounds were synthesized through an asymmetric transfer hydrogenation reaction from achiral purine derivatives. Up to 97% ee and good to excellent yields were achieved under mild conditions through short reaction steps. The present report suggests an efficient process to acquire tenofovir and its analogues.