利巴韦林杂质G | 39030-43-8

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: 利巴韦林杂质G
• 中文别名: 异利巴韦林（利巴韦林杂质G）
• 英文名称: 1-β-D-ribofuranosyl-1H-1,2,4-triazole-5-carboxamide
• 英文别名: 2-(β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide；2-β-D-ribofuranosyl-2H-[1,2,4]triazole-3-carboxylic acid amide；1-β-D-Ribofuranosyl-<1,2,4>triazol-5-carboxamid；1-β-D-Ribofuranosyl-1.2.4-triazol-5-carboxamid；β-D-Ribofuranosyl-1.2.4-triazol-5-carboxamid；1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-5-carboxamide；2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• CAS: 39030-43-8
• 化学式: C₈H₁₂N₄O₅
• 分子量: 244.207
• InChiKey: HAMRZKKGAOJPDG-AFCXAGJDSA-N

物化性质

• 熔点：
  58-60°C
• 沸点：
  639.8±65.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 1-(2',3',3''-tri-O-benzoyl-apio-β-D-furanosyl)triazole-5-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 生成 利巴韦林杂质G
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Glycosylhydrazine, 4. <i>1H</i> ‐1,2,4‐Triazol‐nucleoside — Synthese von Virazol
  作者：Richard R. Schmidt、Dieter Heermann

  DOI：10.1002/cber.19811140814

  日期：1981.8

  Aus den Ribosehydrazonen 1a,b und den Oxalsäure-Derivaten 2 und 13 wurden regio- und diastereoselektiv in wenigen Stufen Virazol (11) und das isomere 1-β-D-Ribofuranosyl-1H-1,2,4-triazol-5-carboxamid (19) erhalten. Die hier verfolgte aufbauende Synthesemethode wurde auch zur Herstellung des unsubstituierten Triazol-nucleosids 20 angewandt. Bei dieser Methode werden beim Triazolringschluß in einem Reaktionsschritt

  AUS巢穴Ribosehydrazonen 1a中，b UND巢穴Oxalsäure-Derivaten 2 UND 13 wurden区域选择性UND diastereoselektiv在wenigen Stufen Virazol（11）UND DAS isomere 1-β-d-呋喃核糖基1H -1,2,4-三唑-5-甲酰胺（19）淡化。合成方法未取代三唑核苷20碱基。《欧洲复兴》和《β-形变概论》中的“三分法”。
• 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.
• US3991078A
  申请人：——

  公开号：US3991078A

  公开（公告）日：1976-11-09