3-(β-D-ribosyl)-2,4-quinazolinedione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(β-D-ribosyl)-2,4-quinazolinedione
• 英文别名: 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-quinazoline-2,4-dione
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: UFTHBPMHABUVEK-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  卡培他滨杂质25 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 3 A molecular sieve 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 192.0h， 生成 3-(β-D-ribosyl)-2,4-quinazolinedione
  参考文献：
  名称：

  Base-modified nucleosides from carbohydrate derived oxazolidinethiones: a five-step process

  摘要：

  Starting from unprotected carbohydrates, base-modified nucleosides could be reached in four steps through the condensation of anthranilic acid with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00357-4

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.
• Small libraries of fused quinazolinone-sugars. Access to quinazolinedione nucleosides
  作者：Jolanta Girniene、Guillaume Apremont、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/j.tet.2004.01.032

  日期：2004.3

  Unprotected carbohydrates can readily be converted into base-modified nucleosides and deoxynucleosides through a short sequence involving the condensation of anthranilic acid derivatives with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2004 Elsevier Ltd. All rights reserved.
• Base-modified nucleosides from carbohydrate derived oxazolidinethiones: a five-step process
  作者：Jolanta Girniene、David Gueyrard、Arnaud Tatibouët、Algirdas Sackus、Patrick Rollin

  DOI：10.1016/s0040-4039(01)00357-4

  日期：2001.4

  Starting from unprotected carbohydrates, base-modified nucleosides could be reached in four steps through the condensation of anthranilic acid with a suitably protected sugar-derived 2-alkylthio-1,3-oxazoline. (C) 2001 Elsevier Science Ltd. All rights reserved.