2',3'-didehydro-2',3'-dideoxy-4'-C-methyladenosine | 152540-78-8

• 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: 2',3'-didehydro-2',3'-dideoxy-4'-C-methyladenosine
• 英文别名: [(2R,5S)-2-(6-aminopurin-9-yl)-5-methyl-2H-furan-5-yl]methanol
• CAS: 152540-78-8
• 化学式: C₁₁H₁₃N₅O₂
• 分子量: 247.257
• InChiKey: YIDBICIOHZXQHR-HQJQHLMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 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：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',3'-didehydro-2',3'-dideoxy-4'-C-methyladenosine 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以68%的产率得到2',3'-dideoxy-4'-methyladenosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385
• 作为产物：
  描述：

  9-(4-C-methyl-β-D-ribofuranosyl)-adenine 在 咪唑 、 1,3-二甲基-2-苯基-2-磷杂咪唑烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.84h， 生成 2',3'-didehydro-2',3'-dideoxy-4'-C-methyladenosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385

文献信息

• Asymmetric Synthesis of Oxygen Heterocycles via Pd-Catalyzed Dynamic Kinetic Asymmetric Transformations: Application to Nucleosides
  作者：Barry M. Trost、Brian S. Brown、Ernest J. McEachern、Oliver Kuhn

  DOI：10.1002/chem.200304949

  日期：2003.9.22

  the case of 2-phenylbutadiene monoepoxide, easily available from phenacyl chloride and vinylmagnesium bromide, the reaction proceeds by kinetic resolution. A model to rationalize the result is presented. The bis-olefin products are ideal substrates for the Ru catalyzed ring closing metathesis. In this way, five-, six-, and seven-membered oxygen heterocycles are readily available enantiomerically pure

  外消旋丁二烯和异戊二烯单环氧化物在手性钯催化剂和硼助催化剂的存在下与不饱和醇反应，生成3-烷氧基-4-羟基-1-丁烯和3-烷氧基-4-羟基-3-甲基-1 -丁烯在动态动力学不对称转化中分别具有优异的区域和对映选择性，由此起始环氧化物的两种对映异构体均提供相同的对映异构体产物。在2-苯基丁二烯单环氧化物的情况下，可容易地从苯甲酰氯和乙烯基溴化镁得到，反应通过动力学拆分进行。提出了使结果合理化的模型。双烯烃产品是Ru催化的闭环复分解反应的理想底物。以此方式，对映体纯的五元，六元和七元氧杂环容易获得。通过使用五元环杂环形成不自然和不寻常的核苷，无法用其他方法轻易获得，证明了这一非常简单的两步法的价值。该序列涉及Ru由最初的2，5-二氢呋喃催化的异构化为2，3-二氢呋喃，然后是硒促进的嘧啶或嘌呤碱的添加。该策略的一个优势是可以轻松获得任一对映体系列，这两个对映体系列都有重要的生物学应用。3-二氢呋
• [EN] LINE-1 INHIBITORS AS COGNITIVE ENHANCERS<br/>[FR] INHIBITEURS DE LINE-1 UTILISÉS EN TANT QU'ACTIVATEURS COGNITIFS
  申请人：[en]TRANSPOSON THERAPEUTICS, INC.

  公开号：WO2022256625A1

  公开（公告）日：2022-12-08

  The present disclosure provides methods of enhancing cognition, inhibiting cognitive decline, treating or preventing a cognitive deficit disorder, or treating or preventing Creutzfeldt-Jakob disease (CJD) in a subject in need thereof comprising administering a LINE-1 inhibitor, or a pharmaceutical composition thereof, to the subject.
• Synthesis and Biological Evaluation of 4′-<i>C</i>-Methyl Nucleosides
  作者：Toshiaki Waga、Hiroshi Ohrui、Hiroshi Meguro

  DOI：10.1080/07328319608002385

  日期：1996.1

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.