1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyridinone | 18342-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyridinone
• 英文别名: 1-(2,2,5-Tri-O-benzoyl-β-D-ribofuranosyl)-1,4-dihydropyridin-4-on；1-(2',3',5'-tri-O-benzoyl-beta-D-ribofuranosyl)-4-pyridone；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-oxopyridin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 18342-24-0
• 化学式: C₃₁H₂₅NO₈
• 分子量: 539.541
• InChiKey: RPRRPNSOVAMAHG-BIYDSLDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 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：
  108
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyridinone 在 吡啶 、 N-甲基咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 silver nitrate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of pyridinone ribonucleoside 3′-O-phosphoramidites and their incorporation into oligoribonucleotides

  摘要：

  Protected pyridin-2- and pyridin-4-one ribonucleosides 3 and 9 were synthesized using a one-pot reaction of silylated bases with 1-O-acetyl-tri-O-benzoyl-beta-D-ribofuranose (2) in the presence of CF(3)SO(3)SiMe(3) The nucleosides were converted in 4 steps into 3'-O-phosphoramidites 7 and 11 which were incorporated into hammerhead ribozyme substrates using solid-phase phosphoramidite chemistry.

  DOI：

  10.1016/0960-894x(96)00030-3
• 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 、 三甲基(吡啶-4-氧基)硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 以87%的产率得到1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyridinone
  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

• Process for the preparation of nucleosides
  申请人：Schering Aktiengesellschaft

  公开号：US04209613A1

  公开（公告）日：1980-06-24

  In a process for preparing a nucleoside by silylating the corresponding nucleoside base and reacting the silylated base with a 1-O-acyl, 1-O-alkyl, or 1-halogen derivative of a blocked monosaccharide or oligosaccharide in the presence of a catalyst, an improvement comprises silylating the base and reacting the sugar derivative in a single step.

  一种制备核苷的方法，通过硅基化相应的核苷碱并在催化剂存在下将硅基化的碱与被阻断的单糖或寡糖的1-O-酰基、1-O-烷基或1-卤素衍生物反应。改进的方法是将碱硅基化和糖衍生物反应合并为一步。
• Modified Short Interfering Nucleic Acid (siNA) Molecules and Uses Thereof
  申请人：Aligos Therapeutics, Inc.

  公开号：US20220177888A1

  公开（公告）日：2022-06-09

  Disclosed herein are short interfering nucleic acid (siNA) molecules comprising modified nucleotides and uses thereof. The siNA molecules may be double stranded and comprise modified nucleotides selected from 2′-O-methyl nucleotides and 2′-fluoro nucleotides. Further disclosed herein are siNA molecules comprising (a) a phosphorylation blocker, conjugated moiety, or 5′-stabilized end cap; and (b) a short interfering nucleic acid (siNA).

  本文披露了包含修饰核苷酸的短干扰核酸（siNA）分子及其用途。siNA分子可以是双链的，并包括从2'-O-甲基核苷酸和2'-氟核苷酸中选择的修饰核苷酸。本文还披露了包含（a）磷酸化阻断剂、共轭基团或5'-稳定端盖；以及（b）短干扰核酸（siNA）的siNA分子。
• Neues Verfahren zur Herstellung von Nucleosiden
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0003229A1

  公开（公告）日：1979-08-08

  Das Verfahren zur Herstellung eines Nucleosids durch Silylierung der entsprechenden Nucleosidbase und Reaktion dieser silylierten Base mit einem in 1- oder 2-Position durch Acyl, Alkyl oder Halogen substituierten, geschützten Mono-oder Oligosaccharid in Gegenwart eines Katalysators führt die Silylierung der Base, falls erforderlich die Silylierung des Katalysators und die Reaktion mit dem Zuckerderivat in einem Schritt durch.

  通过将相应的核苷碱基硅烷化，并在催化剂存在下使硅烷化碱基与在 1 位或 2 位被酰基、烷基或卤素取代的受保护的单糖或寡糖反应来制备核苷的工艺，一步完成碱基的硅烷化，必要时完成催化剂的硅烷化以及与糖衍生物的反应。
• Vorbrueggen, Helmut; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1279 - 1286
  作者：Vorbrueggen, Helmut、Bennua, Baerbel

  DOI：——

  日期：——
• 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.