4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone | 23220-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone
• 英文别名: 4-hydroxy-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyridin-2-one；4-Hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-pyridon；3-Deazauridin-2',3',5'-tribenzoat；3-Deaza-uridin-tribenzoat；4-Hydroxy-1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2(1H)-pyridinone；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-hydroxy-2-oxopyridin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 23220-74-8
• 化学式: C₃₁H₂₅NO₉
• 分子量: 555.541
• InChiKey: GUEPFYBEHGIHIW-YULOIDQLSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  728.9±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DCM、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以2.28 g的产率得到3-bromo-4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone
  参考文献：
  名称：

  3-取代的3-脱氮胞苷和3-取代的3-脱氮尿苷的合成，抗肿瘤活性和抗病毒活性。

  摘要：

  4-氨基-1-β-D-呋喃呋喃糖基-2（1H）-吡啶酮（3-脱氮胞苷，3）和4-羟基-1-β-D-呋喃呋喃糖基-2（1H）-吡啶酮的新型3-取代类似物（3-deazauridine，4）已被合成并测试其抗肿瘤和抗病毒活性。因此，3的3-氯（9a），3-溴（9b）和3-硝基（9c）类似物以及3-氯（9d），3-溴（9e）和3-硝基（9f）类似物通过标准糖基化程序制备4个。通过卤化4-氨基-2（1H）来制备新型必需杂环4-氨基-3-氯-2（1H）-吡啶酮（7a）和4-氨基-3-溴-2（1H）-吡啶酮（7b） -吡啶酮（5）。必需的杂环化合物4-氨基-3-硝基-2（1H）-吡啶酮（7c），3-氯-4-羟基-2（1H）-吡啶酮（7d），3-溴-4-羟基-2（1H） -吡啶酮（7e），用已知方法由4-羟基-2（1H）-吡啶酮（6）合成4-羟基-3-硝基-2（1H）-吡啶酮（7f）。通过独立合成，1 H

  DOI：

  10.1021/jm00169a032
• 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 、 2,4-二羟基吡啶 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone
  参考文献：
  名称：

  High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

  摘要：

  [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.

  DOI：

  10.1021/jo061885l

文献信息

• Synthesis and Biological Evaluation of 3,3-Difluoropyridine-2,4(1<i>H</i>,3<i>H</i>)-dione and 3-Deaza-3-fluorouracil Base and Nucleoside Derivatives
  作者：Morris J. Robins、Hong Yang、Karl Miranda、Matt A. Peterson、Erik De Clercq、Jan Balzarini

  DOI：10.1021/jm900203h

  日期：2009.5.14

  compounds. Selective reaction of a stabilized Wittig reagent at C4 of the 3,3-difluoro-2,4-dione intermediates gave exocyclic alkenes that underwent hydrogenation accompanied by spontaneous elimination of hydrogen fluoride. Ammonolysis of the exocyclic carbethoxymethyl substituent and ester protecting groups gave 4-(carboxamidomethyl)-3-deaza-3-fluorouridine and its analogues. Grignard additions at C4 of

  新的3-deaza-3-halouracil核苷，包括3-deaza-3-fluorouridine及其2'-deoxy和阿拉伯糖类似物已经通过氟化被保护的前体来制备。所得的3,3-二氟吡啶-2,4（1 H，3 H）-二酮衍生物在大气压下经过钯催化的一个C-F键的氢解，然后脱保护得到3-deaza-3-fluorouracil化合物。稳定的维蒂希试剂在3,3-二氟-2,4-二酮中间体的C4处的选择性反应产生了环外烯烃，该环烯烃经过加氢并自发消除了氟化氢。环外乙氧甲基甲基取代基和酯保护基的氨解得到4-（羧酰胺基甲基）-3-脱氮基-3-氟尿苷及其类似物。在核糖的C4和2'-脱氧3,3-二氟-2,4-二酮中间体的格利雅加成反应，然后脱保护得到3-deaza-3,3-difluoro-4-hydroxy-4-hydroxyd（hydroxyated）urcil nucleosides 。3-flu
• A Novel Nucleophilic Displacement of Benzoate by Sulfur During Thiation of 3-Deazauridine Tribenzoate
  作者：Morris J. Robins、Bruce L. Currie、Roland K. Robins、Arthur D. Broom

  DOI：10.1139/v71-513

  日期：1971.9.15

  β-picoline followed by debenzoylation gave 2-mercapto-1-(2-deoxy-β-D-arabinofuranosyl)pyridine-4-thione-S2 → 2′-cyclonucleoside (2b). Thus, replacement of the heterocyclic oxygens by sulfur followed by a novel nucleophilic displacement of benzoate by mercaptide in the hot basic solution must have occurred.

  3-脱氮尿苷三苯甲酸酯 [4-羟基-1-(2,3,5-三-O-苯甲酰基-β-D-呋喃核糖基)-2-吡啶酮] (1a) 与五硫化二磷在潮湿的 β-甲基吡啶中的硫化脱苯甲酰化得到 2-mercapto-1-(2-deoxy-β-D-arabinofuranosyl)pyridine-4-thione-S2 → 2'-cyclonucleoside (2b)。因此，在热碱性溶液中一定发生了用硫取代杂环氧，然后用硫醇盐对苯甲酸酯进行新的亲核置换。
• MCNAMARA, DENNIS J.;DAN, COOK P.;ALLEN, LOIS B.;KEHOE, MARY J.;HOLLAND, C+, J. MED. CHEM., 33,(1990) N, C. 2006-2011
  作者：MCNAMARA, DENNIS J.、DAN, COOK P.、ALLEN, LOIS B.、KEHOE, MARY J.、HOLLAND, C+

  DOI：——

  日期：——