1-(3-O-acetyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine | 52523-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(3-O-acetyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine
• 英文别名: 1-(5'-deoxy-3'-O-acetyl-β-erythro-pent-4'-enofuranosyl)thymine；1-(3-O-Acetyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)-thymin；O^3'-acetyl-4',5'-didehydro-5'-deoxy-thymidine；1-[(2R,4S)-4-(Acetyloxy)tetrahydro-5-methylene-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedione；[(3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-methylideneoxolan-3-yl] acetate
• CAS: 52523-37-2
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: AVFHSFJOCCTNND-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.39
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-(3-O-acetyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine 在 咪唑 、 氨 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(3-O-tert-butyldimethylsilyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine
  参考文献：
  名称：

  4'，5'-环氧核苷的开环：4'-C-支链核苷的新型立体选择性进入。

  摘要：

  立体选择性合成4'-α-碳取代的核苷已通过4'，5'-不饱和核苷与二甲基二环氧乙烷（DMDO）的环氧化和连续的SnCl（4）促进所得4'，5'-的开环而完成环氧核苷与有机硅试剂。[反应：看文字]

  DOI：

  10.1021/ol020259h
• 作为产物：
  描述：

  3'-O-acetyl-5'-deoxy-5'-iodothymidine 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 乙腈 为溶剂， 以87%的产率得到1-(3-O-acetyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine
  参考文献：
  名称：

  4'，5'-环氧核苷的开环：4'-C-支链核苷的新型立体选择性进入。

  摘要：

  立体选择性合成4'-α-碳取代的核苷已通过4'，5'-不饱和核苷与二甲基二环氧乙烷（DMDO）的环氧化和连续的SnCl（4）促进所得4'，5'-的开环而完成环氧核苷与有机硅试剂。[反应：看文字]

  DOI：

  10.1021/ol020259h

文献信息

• Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections
  申请人：Cheng Yung-chi

  公开号：US09126971B2

  公开（公告）日：2015-09-08

  The present invention relates to novel compounds according to the general formulas I, II, III, IV or V: wherein B is nucleoside base according to the structure: and the remaining variables as defined in the specification, and pharmaceutical compositions comprising the compounds. The compounds are useful interalia as anti-viral agents in viral therapy.

  本发明涉及根据一般式I、II、III、IV或V的新化合物： 其中B是根据以下结构的核苷酸碱基： 以及规范中定义的其余变量，以及包含这些化合物的药物组合物。这些化合物可用作抗病毒剂，用于病毒治疗。
• C4’‐Fluorinated Oligodeoxynucleotides: Synthesis, Stability, Structural Studies
  作者：Yifei Zhou、Kuan Lu、Qiang Li、Chaochao Fan、Chuanzheng Zhou

  DOI：10.1002/chem.202102561

  日期：2021.10.21

  4’-F-Thymidine was synthesized and introduced into DNA strands based on standard solid-phase DNA synthesis protocols. The 4’-F-thymidine in the context of DNA strand is rather stable in neutral buffers. Unlike native deoxyribonucleosides whose ribose predominantly exist in the South conformation, 4’-F-thymidine prefers the North conformation. Incorporation of 4’-F-deoxyribonucleoside into nucleic acids

  4'-F-胸苷是根据标准固相 DNA 合成方案合成并引入 DNA 链的。DNA 链中的 4'-F-胸苷在中性缓冲液中相当稳定。与核糖主要存在于南构象的天然脱氧核糖核苷不同，4'-F-胸苷更喜欢北构象。将 4'-F-脱氧核糖核苷掺入核酸代表了一种先进的方法来调节局部结构，从而调节核酸的功能。
• Tong, W.; Agback, P.; Chattopadhyaya, J., Acta Chemica Scandinavica, 1993, vol. 47, # 2, p. 145 - 156
  作者：Tong, W.、Agback, P.、Chattopadhyaya, J.

  DOI：——

  日期：——
• Nucleophilic Substitution at the 4‘-Position of Nucleosides: New Access to a Promising Anti-HIV Agent 2‘,3‘-Didehydro-3‘-deoxy-4‘-ethynylthymidine
  作者：Kazuhiro Haraguchi、Masanori Sumino、Hiromichi Tanaka

  DOI：10.1021/jo060194m

  日期：2006.6.1

  For the synthesis of 2',3'-didehydro-3'-deoxy-4'-ethynylthymidine (8: 4'-Ed4T), a recently reported promising anti-HIV agent, a new approach was developed. Since treatment of 1-(2,5-dideoxy-beta-L-glyceropent4- enofuranosyl) thymine with Pb(OBz) 4 allowed the introduction of the 4'-benzoyloxy leaving group, nucleophilic substitution at the 4'-position became feasible for the first time. Thus, reaction between the 4'-benzoyloxy derivative (14) and Me3SiC CAl(Et) Cl as a nucleophile led to the isolation of the desired 4'-"down"-ethynyl derivative (18) stereoselectively in 62% yield. As an application of this approach, other 4'-substituted nucleosides, such as the 4'-allyl (24a) and 4'-cyano (26a) derivatives, were synthesized using organosilicon reagents. In these instances, pretreatment of 14 with MeAlCl2 was necessary.
• Tocik, Zdenek; Kavenova, Iva; Rosenberg, Ivan, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S76 - S80
  作者：Tocik, Zdenek、Kavenova, Iva、Rosenberg, Ivan

  DOI：——

  日期：——