2',3',5'-tri-O-benzoyl-3-β-D-ribofuranosylimidazo<4,5-b>pyridine | 80354-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',5'-tri-O-benzoyl-3-β-D-ribofuranosylimidazo<4,5-b>pyridine
• 英文别名: tri-O-benzoyl-1-imidazo[4,5-b]pyridin-3-yl-β-D-1-deoxy-ribofuranose；3-<2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl>-3H-imidazo<4.5-b>pyridin；3-β-D-Ribofuranosyl-3H-imidazo<4,5-b>pyridin-2,3,5-tribenzoat
• CAS: 80354-16-1
• 化学式: C₃₂H₂₅N₃O₇
• 分子量: 563.566
• InChiKey: ONEPOGGMOGMWKN-LTGLEFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  118.84
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoyl-3-β-D-ribofuranosylimidazo<4,5-b>pyridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以72%的产率得到1-Deazapurine riboside
  参考文献：
  名称：

  Gupta, P. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 9, p. 817 - 819

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氮杂苯并咪唑 在 硫酸氢铵 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 45.0h， 生成 2',3',5'-tri-O-benzoyl-3-β-D-ribofuranosylimidazo<4,5-b>pyridine
  参考文献：
  名称：

  Gupta, P. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 9, p. 817 - 819

  摘要：

  DOI：

文献信息

• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.