5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose | 160999-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: O-[1,2-isopropylidene-5-benzoate-α-D-xylofuranosyl] 1H-imidazole-1-carbothioate；5-O-benzoyl-1,2-isopropylidene-3-O-imidazolylthiocarbonyl-α-D-xylofuranose；[(3aR,5R,6S,6aR)-6-(imidazole-1-carbothioyloxy)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 160999-15-5
• 化学式: C₁₉H₂₀N₂O₆S
• 分子量: 404.444
• InChiKey: PCYYNZOCAQDOPW-JYYAWHABSA-N

物化性质

• 沸点：
  535.5±60.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose 在 盐酸 、 三乙基硅烷 、 三甲基氯硅烷 、 18-冠醚-6 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.0h， 生成 4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 以 吡啶 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5

文献信息

• Visible Light Photocatalytic Reduction of<i>O</i>-Thiocarbamates: Development of a Tin-Free Barton-McCombie Deoxygenation Reaction
  作者：Ludwig Chenneberg、Alexandre Baralle、Marion Daniel、Louis Fensterbank、Jean-Philippe Goddard、Cyril Ollivier

  DOI：10.1002/adsc.201400729

  日期：2014.9.15

  The Barton–McCombie deoxygenation is one of the most important transformations in the toolbox of organic chemists which has been the subject of a number of methodological developments. In this study, we report a photocatalyzed redox deoxygenation of secondary and tertiary alcohols from thiocarbamate precursors under visible light activation. The iridium complex Ir(ppy)3 proved to be the most efficient

  Barton–McCombie脱氧是有机化学家工具箱中最重要的转变之一，这已成为许多方法学发展的主题。在这项研究中，我们报告了在可见光激活下从硫代氨基甲酸酯前体对仲醇和叔醇进行光催化的氧化还原脱氧。在Hünig碱作为牺牲电子供体的情况下，铱络合物Ir（ppy）3被证明是最有效的催化剂。提出了基于荧光猝灭实验和循环伏安法的机理研究。
• NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Chen James M.

  公开号：US20100104532A1

  公开（公告）日：2010-04-29

  The invention provides unsaturated phosphonates of Formula I or a tautomer or pharmaceutically accepatble salt thereof, as described herein, as well as pharmaceutical compositions comprising the compounds, and therapeutic methods comprising administering the compounds. The compounds have anti-viral properties and are useful for treating viral infections (e.g. HCV) in animals (e.g. humans).

  本发明提供了公式I或其互变异构体或药学上可接受的盐的不饱和膦酸酯，以及包含这些化合物的制药组合物和包括给予这些化合物的治疗方法。这些化合物具有抗病毒性质，适用于治疗动物（如人类）的病毒感染（例如HCV）。
• Deoxygenation of 5-O-benzoyl-1,2-isopropylidene-3-O-imidazolylthiocarbonyl-α-d-xylofuranose using dimethyl phosphite: an efficient alternate method towards a 3′-deoxynucleoside glycosyl donor
  作者：Ivan Zlatev、Jean-Jacques Vasseur、François Morvan

  DOI：10.1016/j.tetlet.2008.03.079

  日期：2008.5

  An efficient radical deoxygenation reaction of thiocarbonylimidazolyl activated glycoside analogue using dimethyl phosphite as hydrogen source and radical chain carrier was performed as a key step in a multi step synthesis towards a common 3-deoxy glycosyl donor for 3'-deoxynucleosides. This method has safety and cost advantages compared to the generally used radical reduction reagents. (c) 2008 Elsevier Ltd. All rights reserved.
• US8324179B2
  申请人：——

  公开号：US8324179B2

  公开（公告）日：2012-12-04
• [EN] NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT<br/>[FR] ANALOGUES NUCLÉOSIDIQUES POUR TRAITEMENT ANTIVIRAL
  申请人：GILEAD SCIENCES INC

  公开号：WO2008100447A2

  公开（公告）日：2008-08-21

  [EN] The invention provides unsaturated phosphonates of Formula I or a tautomer or pharmaceutically accepatble salt thereof, as described herein, as well as pharmaceutical compositions comprising the compounds, and therapeutic methods comprising administering the compounds. The compounds have anti-viral properties and are useful for treating viral infections (e.g. HCV) in animals (e.g. humans).
  [FR] La présente invention concerne des phosphonates insaturés de formule (I) ou un tautomère ou un sel pharmaceutiquement acceptable de ceux-ci, ainsi que des compositions pharmaceutiques comportant les composés, et des procédés thérapeutiques comprenant l'administration des composés. Les composés présente des propriétés antivirales et sont utiles pour traiter des infections (par exemple, le VHC) chez des animaux (par exemple, des humains).