1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole | 24807-04-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(1,2,4-triazol-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 24807-04-3
• 化学式: C₂₈H₂₃N₃O₇
• 分子量: 513.507
• InChiKey: AOTIOYWDKQYVFY-ZGFBMJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole 在 甲醇 、 氨 作用下， 生成 1-(β-D-ribofuranosyl)-1H-1,2,4-triazol
  参考文献：
  名称：

  [EN] RIBAVIRIN ANALOG AND USE THEREOF AS EMBEDDING GROUP
  [FR] ANALOGUE DE RIBAVIRINE ET SON UTILISATION COMME GROUPE D'ENROBAGE
  [ZH] 三氮唑核苷类似物及其作为嵌入基团的应用

  摘要：

  本发明公开了三氮唑核苷类似物及其作为嵌入基团在RNAi中的应用，具体公开了式(Z)所示化合物。

  公开号：

  WO2023155909A1
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 1-(三甲硅基)-1H-1,2,4-三唑 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole
  参考文献：
  名称：

  [EN] RIBAVIRIN ANALOG AND USE THEREOF AS EMBEDDING GROUP
  [FR] ANALOGUE DE RIBAVIRINE ET SON UTILISATION COMME GROUPE D'ENROBAGE
  [ZH] 三氮唑核苷类似物及其作为嵌入基团的应用

  摘要：

  本发明公开了三氮唑核苷类似物及其作为嵌入基团在RNAi中的应用，具体公开了式(Z)所示化合物。

  公开号：

  WO2023155909A1

文献信息

• Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255
  作者：Vorbrueggen, Helmut、Krolikiewicz, Konrad、Bennua, Baerbel

  DOI：——

  日期：——
• 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.