1,2-di-O-acetyl-3-azido-3-deoxy-5-O-benzoyl-β-D-ribofuranose | 103597-08-6

• 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-azido-3-deoxy-5-O-benzoyl-β-D-ribofuranose
• 英文别名: 1,2-di-O-acetyl-3-azido-5-O-benzoyl-3-deoxy-β-D-ribofuranose；3-azido-1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-β-D-ribofuranose
• CAS: 103597-08-6
• 化学式: C₁₆H₁₇N₃O₇
• 分子量: 363.327
• InChiKey: NLRNMHPVJWQBIY-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  136.89
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3-azido-3-deoxy-5-O-benzoyl-β-D-ribofuranose 在 copper(l) iodide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 3'-deoxy-3'-[4-(3-chloropropyl)-1,2,3-triazol-1-yl]-5-methyluridine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine

  摘要：

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.

  DOI：

  10.1080/15257770.2013.847957
• 作为产物：
  描述：

  5-O-benzoyl-α-D-xylofuranose 在 吡啶 、 sodium azide 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 1,2-di-O-acetyl-3-azido-3-deoxy-5-O-benzoyl-β-D-ribofuranose
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine

  摘要：

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.

  DOI：

  10.1080/15257770.2013.847957

文献信息

• Synthesis and Antiviral Evaluation of Azt Analogues with A Spacer Arm Between Glucidic and Base Moieties. Part II
  作者：Vincent Roy、Rachida Zerrouki、Pierre Krausz、Géraldine Laumond、Anne Marie Aubertin

  DOI：10.1080/15257770701426153

  日期：2007.6.15

  This article describes the synthesis of a series of AZT analogues bearing an acyclic chain between the sugar and the base moieties is described. These new compounds were readily obtained using microwave irradiation. The compounds were characterized by (1)H NMR and IR spectroscopy. Antiviral (HIV-1) properties of these compounds were examined.

  本文描述了一系列在糖和碱基部分之间带有无环链的AZT类似物的合成。这些新化合物很容易通过微波辐射获得。通过（1）1 H NMR和IR光谱对化合物进行表征。检查了这些化合物的抗病毒（HIV-1）特性。
• Synthesis of some modified 2′-5′-linked oligoriboadenylates of 2-5A core
  作者：G. M. Visser、M. Tromp、J. van Westrenen、O. Schipperus、J. H. van Boom

  DOI：10.1002/recl.19861050303

  日期：——

  The synthesis of three analogues of 2′-5′-linked oligoriboadenylates is reported. Two trimers, having at the 2′-end a 3′-amino- (or 3′-tetradecanamido)-3′-deoxy-riboadenosine, were assembled via a phosphotriester approach. In the same way, we also prepared a tetramer carrying at the 2′-end β-L-riboadenosine instead of β-D-riboadenosine. The non-terminal building unit 3′,5′-O-(tetraisopropyldisiloxane-1

  报道了2'-5'-连接的寡聚腺苷酸的三种类似物的合成。通过磷酸三酯方法组装了在2'端具有3'-氨基-（或3'-十四烷酰胺基）-3'-脱氧核糖核苷的三聚体。同样，我们还制备了在2'端带有β-L-核糖腺苷而不是β-D-核糖腺苷的四聚体。使用磷酸化剂2-氯苯基-O，O-bis（）将非末端构建单元3'，5'- O-（四异丙基二硅氧烷-1,3-二基）-N 6-苯并腺苷与适当保护的改性核糖腺苷偶联。1-苯并三唑基）磷酸盐。通过氨解作用，然后用氟离子处理，从中间三聚体和四聚体上除去所有保护基。