2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole | 63202-27-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole
• CAS: 63202-27-7
• 化学式: C₁₈H₂₀N₂O₇
• 分子量: 376.366
• InChiKey: GTCKIGAZGVZGSJ-BRSBDYLESA-N

物化性质

• 沸点：
  525.2±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105.95
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole 在 对甲苯磺酸 作用下， 以 氯苯 为溶剂， 生成 2-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)indazole 、 1-(2',3',5'-tri-O-acetyl-α-D-ribofuranosyl)indazole 、 Acetic acid (2S,3S,4S,5R)-4-acetoxy-5-acetoxymethyl-2-indazol-1-yl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Transglycosylation of β-D-RIbofuranosylindazoles

  摘要：

  Irreversible, acid-catalyzed 2 --> 1 transglycosylation reactions of fully acetylated beta-D-ribofuranosylindazoles were studied applying HPLC analysis. Results so obtained support the intermolecular mechanism of transglycosylation via a 1,2-diglycosylindazole intermediate and are compared to those of the purine series.

  DOI：

  10.1080/15257779508014654
• 作为产物：
  描述：

  吲唑 在 吡啶 、 甲醇 、 氨 、 对甲苯磺酸 作用下， 反应 36.0h， 生成 2-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)indazole
  参考文献：
  名称：

  Transglycosylation of β-D-RIbofuranosylindazoles

  摘要：

  Irreversible, acid-catalyzed 2 --> 1 transglycosylation reactions of fully acetylated beta-D-ribofuranosylindazoles were studied applying HPLC analysis. Results so obtained support the intermolecular mechanism of transglycosylation via a 1,2-diglycosylindazole intermediate and are compared to those of the purine series.

  DOI：

  10.1080/15257779508014654

文献信息

• Nucleoside synthesis: A systematic study of the influence of the nature and stereochemistry of d-aldopentofuranoses, and the effect of the substituent at C-2, in the acid-catalyzed fusion-reaction with indazole
  作者：Bernard L. Kam、Jean-Louis Barascut、Jean-Louis Imbach

  DOI：10.1016/0008-6215(80)90009-9

  日期：1980.1

  the nature and stereochemistry of the d -aldopentofuranose and the effect of the substituent at C-2 have been investigated by using indazole as a model heterocycle. The results obtained show that the nature and stereochemistry of the starting, per-O-acetylated d -aldopentofuranose have no significant effect upon the product distribution of the acid-catalyzed fusion-reaction. The use of a sugar lacking

  摘要报道了酸催化熔融反应的系统研究。通过使用吲唑作为模型杂环研究了d-醛糖戊呋喃糖的性质和立体化学的影响以及C-2上取代基的影响。获得的结果表明，起始的，过-O-乙酰化的d-醛糖戊呋喃糖的性质和立体化学对酸催化的融合反应的产物分布没有显着影响。然而，使用在C-2处缺少参与基团的糖表明，缺乏参与会增加cis-1'，2'-核苷的比例，并讨论了所涉及的机理。在所有情况下，结果表明产物的分布取决于它们的相对热力学稳定性。
• Boronic Acid-Catalyzed Regio- and Stereoselective <i>N</i>-Glycosylations of Purines and Other Azole Heterocycles: Access to Nucleoside Analogues
  作者：Shrey P. Desai、Giorgos Yatzoglou、Julia A. Turner、Mark S. Taylor

  DOI：10.1021/jacs.3c14434

  日期：2024.2.21

  In the presence of an arylboronic acid catalyst, azole-type heterocycles, including purines, tetrazoles, triazoles, indazoles, and benzo-fused congeners, undergo regio- and stereoselective N-glycosylations with furanosyl and pyranosyl trichloroacetimidate donors. The protocol, which does not require stoichiometric activators, specialized leaving groups, or drying agents, provides access to nucleoside

  在芳基硼酸催化剂存在下，唑类杂环，包括嘌呤、四唑、三唑、吲唑和苯并稠合同系物，与呋喃糖基和吡喃糖基三氯乙酰亚氨酸供体发生区域和立体选择性N-糖基化。该方案不需要化学计量的激活剂、专门的离去基团或干燥剂，提供了核苷类似物的途径，并能够实现含唑药剂的后期N-糖基化。已经提出了一种涉及有机硼催化剂同时激活糖基供体和受体的机制，并得到动力学分析和计算模型的支持。