7-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-3H-嘌呤-6-酮 | 10280-01-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 7-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-3H-嘌呤-6-酮
• 英文名称: 6-Hydroxy-7-<β-ribofuranosyl>-purin
• 英文别名: 7-(ss-D-Ribofuranosyl)-hypoxanthin；7-(β-D-Ribofuranosyl)-hypoxanthin, 7-(β-D-Ribofuranosyl)-3-oxo-purin；7-β-D-Ribofuranosyl-hypoxanthin；7-β-D-ribofuranosyl-1,7-dihydro-purin-6-one；7-beta-Ribofuranosylhypoxanthine；7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 10280-01-0
• 化学式: C₁₀H₁₂N₄O₅
• 分子量: 268.229
• InChiKey: MTBCDJLBNPJBFZ-KQYNXXCUSA-N

物化性质

• 沸点：
  797.9±60.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Bis-trimethylsilyl-hypoxanthin 、 四乙酰核糖 生成 7-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-3H-嘌呤-6-酮
  参考文献：
  名称：

  MAURINSH, YU. A.;YANSONS, YA. YA.;PAEHGLE, R. A.;LIDAK, M. YU., KOMPONENTY NUKLEIN. KISLOT: 8 BCEC. SIMP. PO TSELENAPRAVL. IZYSKANIYU LEK+

  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.
• PURINE NUCLEOSIDE PHOSPHORYLASE AS ENZYMATIC ACTIVATOR OF NUCLEOSIDE PRODRUGS
  申请人：The UAB Research Foundation

  公开号：EP2331115B3

  公开（公告）日：2018-12-05