1-[(1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea | 158262-98-7

• 分子结构分类: 有机化合物
• 英文名称: 1-[(1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea
• CAS: 158262-98-7
• 化学式: C₁₄H₂₂N₂O₅
• 分子量: 298.339
• InChiKey: XFEZWAIJTRUBGB-YLWLOCCTSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-[(1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea 在 盐酸 、 ammonium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.16h， 生成 (1'S,2'R)-1-<2-(Hydroxymethyl)cyclopropyl>thymine
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047
• 作为产物：
  描述：

  (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carbonyl azide 在 吡啶 、 氨 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 1-[(1S,2R)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-cyclopropyl]-3-((E)-3-methoxy-2-methyl-acryloyl)-urea
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047

文献信息

• Asymmetric Synthesis of Cyclopropyl Carbocyclic Nucleosides
  作者：Y. F. Zhao、M. G. Lee、T. -F. Yang、B. K. Chun、J. F. Du、R. F. Schinazi、C. K. Chu

  DOI：10.1080/15257779508012367

  日期：1995.5.1

  Abstract A number of nucleosides have been synthesized as potential antiviral and antitumor agents.1 More recently, various dideoxynucleosides have been synthesized and found to be potent anti-HIV agents.2 As a part of our drug discovery program for the treatment of HIV and HBV, we have initiated to synthesize cyclopropyl carbocyclic nucleosides as potential antiviral agents. Several papers regarding

  摘要已合成了许多核苷作为潜在的抗病毒药和抗肿瘤药。1最近，已合成了多种双脱氧核苷，发现它们是有效的抗HIV药物。2作为我们用于治疗HIV和HBV的药物发现计划的一部分，我们已经开始合成环丙基碳环核苷作为潜在的抗病毒剂。关于环丙基碳环核苷合成的几篇论文已经出现在文献中。3-5然而，它们都被报告为外消旋混合物。在此摘要中，我们希望报告由旋光性常用中间体6和11不对称合成环丙基碳环核苷的方法。