O^5'-(4-methyl-benzoyl)-thymidine | 35898-26-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: O^5'-(4-methyl-benzoyl)-thymidine
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 35898-26-1
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: LTIXRVXKVYJQIJ-RRFJBIMHSA-N

物化性质

• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O^5'-(4-methyl-benzoyl)-thymidine 在 咪唑 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3'-O-(叔丁基二甲基硅烷基)胸苷
  参考文献：
  名称：

  Facile Preparation of Protected Furanoid Glycals from Thymidine

  摘要：

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.

  DOI：

  10.1021/jo970947s
• 作为产物：
  描述：

  对甲基苯甲酰氯 、 beta-胸苷 在 吡啶 作用下， 生成 O^5'-(4-methyl-benzoyl)-thymidine
  参考文献：
  名称：

  Non-standard nucleobases implementing the isocytidine and isoguanosine hydrogen bonding patterns

  摘要：

  这项发明提供了物质组合，当纳入寡核苷酸时，向沃森-克里克配对几何结构中的互补链呈现一种氢键模式，该模式与腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶呈现的模式不同。更具体地说，该发明揭示并声明了一种物质组合，其呈现与异胞嘧啶和异鸟嘌呤核碱基相同的氢键结合模式，但不具有不利的互变异构形式，不会从其糖中解离，并且不会像异胞嘧啶和异鸟嘌呤那样轻易地或强烈地进行主沟相互作用。

  公开号：

  US07741294B1

文献信息

• [EN] SYNTHESIS OF beta-L-2-DEOXY NUCLEOSIDES<br/>[FR] SYNTHESE DE NUCLEOSIDES 20050113See references of EP 1639121A4
  申请人：IDENIX CAYMAN LTD

  公开号：WO2005003374A2

  公开（公告）日：2005-01-13

  An improved process for the preparation of 2'-modified nucleosides and 2'-deoxy-nucleosides, such as, β-L-2'-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2'-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2'­ anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2'-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2'-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2'-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的制备2'-修饰核苷和2'-脱氧核苷（例如β-L-2'-脱氧胸腺嘧啶（LdT））的方法。特别是，改进的方法是针对合成2'-脱氧核苷的，可以利用不同的起始材料，但是通过氯代糖中间体或2,2'-无水-1-呋喃核碱中间体进行。当使用2,2'-无水-1-呋喃基中间体时，采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚）引起分子内置换反应并形成所需的核苷产物，产率较高。本发明的另一种替代方法利用2,2'-无水-1-呋喃基中间体而不使用隔离剂，可以获得产率较高的2'-脱氧核苷。根据本发明制备的化合物可以用作其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• SYNTHESIS OF BETA -L-2-DEOXY NUCLEOSIDES
  申请人：Idenix (Cayman) Limited

  公开号：EP1639121A2

  公开（公告）日：2006-03-29
• EP1639121A4
  申请人：——

  公开号：EP1639121A4

  公开（公告）日：2008-04-16
• Facile Preparation of Protected Furanoid Glycals from Thymidine
  作者：Melissa A. Cameron、Sarah B. Cush、Robert P. Hammer

  DOI：10.1021/jo970947s

  日期：1997.12.1

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.
• Non-standard nucleobases implementing the isocytidine and isoguanosine hydrogen bonding patterns
  申请人：——

  公开号：US07741294B1

  公开（公告）日：2010-06-22

  This invention provides compositions of matter that, when incorporated into an oligonucleotide, present to a complementary strand in a Watson-Crick pairing geometry a pattern of hydrogen bonds that is different from the pattern presented by adenine, guanine, cytosine, and thymine. Most specifically, this invention discloses and claims compositions of matter that present the same hydrogen bonding patterns as the isocytidine and isoguanosine nucleobases, but do not have unfavorable tautomeric forms, do not become disassociated from their sugar, and do not make major groove interactions, as much, as easily, or as strongly as isocytidine and isoguanosine.

  这项发明提供了物质组合，当纳入寡核苷酸时，向沃森-克里克配对几何结构中的互补链呈现一种氢键模式，该模式与腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶呈现的模式不同。更具体地说，该发明揭示并声明了一种物质组合，其呈现与异胞嘧啶和异鸟嘌呤核碱基相同的氢键结合模式，但不具有不利的互变异构形式，不会从其糖中解离，并且不会像异胞嘧啶和异鸟嘌呤那样轻易地或强烈地进行主沟相互作用。