[(3R,5R)-2-benzoyloxy-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate | 744217-13-8

• 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: [(3R,5R)-2-benzoyloxy-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 744217-13-8
• 化学式: C₃₀H₃₆N₂O₈Si
• 分子量: 580.71
• InChiKey: PERSKYOPXOVDEM-JGTWLXFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3R,5R)-2-benzoyloxy-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate 在 吡啶 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 sodium methylate 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 festinavir
  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
• 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 、 氨 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 41.0h， 生成 [(3R,5R)-2-benzoyloxy-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
  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

• 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.
• An Alternative Synthetic Method for 4′-C-Ethynylstavudine by Means of Nucleophilic Substitution of 4′-Benzoyloxythymine Nucleoside
  作者：Kazuhiro Haraguchi、Masanori Sumino、Hiromichi Tanaka

  DOI：10.1080/15257770701503969

  日期：2007.11.26

  For the synthesis of 2,3'-didehydro-3'-deoxy-4'-C-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-glycero-pent-4-enofuranosyl)thymine with Pb(OBz)(4) allowed the introduction of a 4'-benzoyloxy leaving group, nucleophilic substitution at the 4'-position became feasible, for the first time. Thus, reaction between the 4'-benzoyloxy derivative (H) and Me3SiC CAl(Et)Cl as a nucleophile led to the isolation of the desired 4'-"down"-ethynyl derivative (15) stereoselectively in 62 % yield.
• 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。