| 935397-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 935397-93-6
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: PFHLDAFDOVPBNO-DYSFYUKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 N-碘代丁二酰亚胺 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 3-O-benzyl-2-C-carbmethoxyazidomethyl-2-deoxy-5,6-isopropylidine-β-D-mannofuranosyl azide
  参考文献：
  名称：

  Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes

  摘要：

  alpha-Amino gamma-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused alpha-amino gamma-lactam and gamma-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.022

文献信息

• Ring opening of activated cyclopropanes with NIS/NaN3: synthesis of C-1 linked pseudodisaccharides
  作者：Shrutisagar Dattatraya Haveli、Sudipta Roy、Vibha Gautam、Ketan C. Parmar、Srinivasan Chandrasekaran

  DOI：10.1016/j.tet.2013.11.005

  日期：2013.12

  NIS/NaN3 mediated ring opening of various donor–acceptor cyclopropanes has been investigated. The study shows the necessity of the donor oxygen lone pair in such ring opening reactions. This methodology has been utilized in the synthesis of C-1 linked pseudodisaccharides through the use of click chemistry.

  已经研究了NIS / NaN 3介导的各种供体-受体环丙烷的开环。研究表明在这种开环反应中需要供体氧孤对。通过使用点击化学，该方法已用于合成C-1连接的假二糖。
• Synthesis of Unnatural C-2 Amino Acid Nucleosides Using NIS-Mediated Ring Opening of 1,2-Cyclopropane Carboxylated Sugar Derivatives
  作者：Srinivasan Chandrasekaran、Shrutisagar Haveli、Sudipta Roy

  DOI：10.1055/s-0028-1087545

  日期：2009.2

  We have developed a general and efficient method for the stereoselective construction of pyrimidine-based pyranosyl C-2 amino acid nucleosides using NIS-mediated ring opening of 1,2-cyclopropanated sugar derivatives. This methodology has been successfully extended to the synthesis of furanosyl nucleosides, Which have potential applications in the development of novel, nontoxic antifungal therapeutics

  我们开发了一种通用且有效的方法，用于使用 NIS 介导的 1,2-环丙烷化糖衍生物的开环立体选择性构建基于嘧啶的吡喃糖基 C-2 氨基酸核苷。该方法已成功扩展到呋喃糖核苷的合成，其在新型无毒抗真菌疗法的开发中具有潜在应用。