1-(3-O-acetyl-2,5-dideoxy-β-L-glycero-pent-4-enofuranosyl)thymine | 128070-96-2

• 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-L-glycero-pent-4-enofuranosyl)thymine
• 英文别名: [(3R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-methylideneoxolan-3-yl] acetate
• CAS: 128070-96-2
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: AVFHSFJOCCTNND-NXEZZACHSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

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-L-glycero-pent-4-enofuranosyl)thymine 在 氨 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 1-(2,5-dideoxy-β-L-glycero-pent-4-enofuranosyl)thymine
  参考文献：
  名称：

  Nucleophilic Substitution at the 4‘-Position of Nucleosides: New Access to a Promising Anti-HIV Agent 2‘,3‘-Didehydro-3‘-deoxy-4‘-ethynylthymidine

  摘要：

  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.

  DOI：

  10.1021/jo060194m
• 作为产物：
  描述：

  1-(3-O-acetyl-2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以90%的产率得到1-(3-O-acetyl-2,5-dideoxy-β-L-glycero-pent-4-enofuranosyl)thymine
  参考文献：
  名称：

  Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections

  摘要：

  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。

  公开号：

  US09126971B2

文献信息

• Addition of carbon radicals to 4′,5′-unsaturated uracilnucleosides by the use of organoselenium reagents: A new stereoselective entry to CC bond formation at the 5′-position
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(00)94378-8

  日期：1990.1
• HARAGUCHI, KAZUHIRO;TANAKA, HIROMICHI;MIYASAKA, TADASHI, TETRAHEDRON LETT., 31,(1990) N, C. 227-230
  作者：HARAGUCHI, KAZUHIRO、TANAKA, HIROMICHI、MIYASAKA, TADASHI

  DOI：——

  日期：——