1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-α,β-D-ribofuranose | 142823-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-α,β-D-ribofuranose
• 英文别名: 1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-D-α,β-xylofuranose；(3R,5S)-5-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-2,3-diyl diacetate；1,2-di-O-acetyl-5-O-(4-methylbenzoyl)-3-deoxy-D-ribofuranose；[(2S,4R)-4,5-diacetyloxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 142823-65-2
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: CPSZOHJXTZTXFQ-BTPDTDQASA-N

物化性质

• 沸点：
  437.1±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-α,β-D-ribofuranose 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 sodium ethanolate 、 六甲基二硅氮烷 作用下， 反应 25.5h， 生成 3-脱氧胞苷
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162
• 作为产物：
  描述：

  alpha-D-呋喃木糖 在 4-二甲氨基吡啶 、 甲酸 、 偶氮二异丁腈 、 硫酸 、 三正丁基氢锡 作用下， 以 吡啶 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 1,2-di-O-acetyl-3-deoxy-5-O-(4-methylbenzoyl)-α,β-D-ribofuranose
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162

文献信息

• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS<br/>[FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES UTILISÉS COMME AGONISTES STING
  申请人：MERCK SHARP & DOHME

  公开号：WO2019125974A1

  公开（公告）日：2019-06-27

  A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类具有通用公式（I）的多环化合物的类别，其中Base1，Base2，Y，Za，Xa，Xa1，Xb，Xb1，Xc，Xc1，Xd，Xd1，R1，R1a，R2，R2a，R3，R4，R4a，R5，R6，R6a，R7，R7a，R8，R8a和R9按本说明书中定义，可能对作为I型干扰素产生的诱导剂特别有用，具体作为STING激活剂。还提供了合成和使用化合物的过程。
• Chain-Terminating and Clickable NAD⁺Analogues for Labeling the Target Proteins of ADP-Ribosyltransferases
  作者：Yan Wang、Daniel Rösner、Magdalena Grzywa、Andreas Marx

  DOI：10.1002/anie.201404431

  日期：2014.7.28

  of PAR. Herein, we report new NAD+ analogues that are efficiently processed by wild‐type ARTs and lead to chain termination owing to a lack of the required hydroxy group, thereby significantly reducing the complexity of the protein modification. Due to the presence of an alkyne group, these NAD+ analogues allow subsequent manipulations by click chemistry for labeling with dyes or affinity markers.

  ADP-核糖基转移酶（ART）使用NAD +作为底物，并通过将多个ADP-核糖单元转移到靶蛋白上形成聚（ADP-核糖），在DNA损伤反应和细胞周期调控等众多生物学过程中发挥重要作用。 （PAR）大小可变的链。努力确定PARylation的直接靶标以及特定的ADP核糖受体位点，都必须解决PAR的复杂性。在本文中，我们报道了新的NAD +类似物，它们可以被野生型ART有效处理，并且由于缺少所需的羟基而导致链终止，从而显着降低了蛋白质修饰的复杂性。由于存在炔基，这些NAD +类似物允许通过点击化学进行后续操作，以使用染料或亲和标记物进行标记。这项研究提供了对ARTs底物范围的深入了解，并可能为进一步研究PAR代谢的化学工具铺平道路。
• Direct SNAr amination of fluorinated imidazo[4,5-c]pyridine nucleosides: efficient syntheses of 3-fluoro-3-deazaadenosine analogs
  作者：Kandasamy Sakthivel、P. Dan Cook

  DOI：10.1016/j.tetlet.2005.03.190

  日期：2005.5

  This paper describes the ready preparation of 3,6-difluoro-3-deazapurine (4,7-difluoroimidazo[4,5-c]pyridine). This novel base was glycosylated under mild conditions using three different ribose sugar analogs. 3,6-Difluoro-3-deazapurine ribonucleoside analogs underwent direct SNAr amination reactions with liquid ammonia to give 3-fluoro-3-deazaadenosine analogs in excellent yield; in contrast, 6-c

  本文介绍了3,6-difluoro-3-deazapurine（4,7-difluoroimidazo [4,5- c ] pyridine）的制备方法。使用三种不同的核糖糖类似物在温和条件下将该新碱基糖基化。3，6-二氟-3-脱氮嘌呤核糖核苷类似物与液氨直接进行S N Ar胺化反应，以极好的收率得到3-氟-3-脱氮杂腺苷类似物。相反，在相似的反应条件下，6-氯-3-氟-3-脱氮嘌呤核苷是惰性的。