1,3-Diribosyluracil | 7561-36-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1,3-Diribosyluracil
• 英文别名: 1,3-di-β-D-ribofuranosyl-1H-pyrimidine-2,4-dione；3-beta-D-Ribofuranosyluridine；1,3-bis[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 7561-36-6
• 化学式: C₁₄H₂₀N₂O₁₀
• 分子量: 376.32
• InChiKey: MGZQQQIXHKHRJT-JXHPLLHESA-N

物化性质

• 沸点：
  734.8±70.0 °C(Predicted)
• 密度：
  1.819±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  181
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3',5'-三乙酰尿苷 在 三丁基膦 、 potassium carbonate 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 10.5h， 生成 1,3-Diribosyluracil
  参考文献：
  名称：

  肌苷和尿苷核苷碱基的糖基化和新的1-（β-D-吡喃葡萄糖基）-肌苷-5'，6“-二磷酸酯的合成。

  摘要：

  研究了糖保护的肌苷和尿苷碱基的糖基和核糖基化，仅在新的糖苷碳上获得了具有β-构型的加合物。使用Mitsunobu方法（用于核糖基化）或通过将1-alpha-溴葡萄糖13与2'，3'，5'-tri-O-乙酰基肌苷直接偶联来实现在肌苷的1-N处糖部分的立体定向插入用于糖基化。1-（β-D-葡萄糖基）-肌苷，被选作环状IDP-核糖的糖基化类似物的起始底物，在伯羟基处被磷酸化，并在分子内焦磷酸盐键的形成中进行测试。

  DOI：

  10.1080/15257770008033052

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.
• Glycosylations of Inosine and Uridine Nucleoside Bases and Synthesis of the New 1-(β-D-Glucopyranosyl)-Inosine-5′, 6″-diphosphate
  作者：Antonia De Capua、Lorenzo De Napoli、Giovanni Di Fabio、Anna Messere、Daniela Montesarchio、Gennaro Piccialli

  DOI：10.1080/15257770008033052

  日期：2000.8

  were investigated, obtaining only adducts with beta-configuration at the new glycosidic carbon; stereospecific insertion of a sugar moiety at the 1-N of inosine was achieved either using a Mitsunobu approach (for ribosylation) or by direct coupling of 1-alpha-bromoglucose 13 with 2',3',5'-tri-O-acetylinosine for glucosylation. 1-(beta-D-glucosyl)-inosine, chosen as starting substrate for glucosylated

  研究了糖保护的肌苷和尿苷碱基的糖基和核糖基化，仅在新的糖苷碳上获得了具有β-构型的加合物。使用Mitsunobu方法（用于核糖基化）或通过将1-alpha-溴葡萄糖13与2'，3'，5'-tri-O-乙酰基肌苷直接偶联来实现在肌苷的1-N处糖部分的立体定向插入用于糖基化。1-（β-D-葡萄糖基）-肌苷，被选作环状IDP-核糖的糖基化类似物的起始底物，在伯羟基处被磷酸化，并在分子内焦磷酸盐键的形成中进行测试。