[(2S,3S,5R)-3-azido-5-(5-formyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate | 1233731-08-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2S,3S,5R)-3-azido-5-(5-formyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1233731-08-2
• 化学式: C₁₂H₁₃N₅O₆
• 分子量: 323.265
• InChiKey: ZLDZHKMNRWSCIV-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3S,5R)-3-azido-5-(5-formyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate 在 Jones reagent 、 氨 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.17h， 生成 3-(3-azido-2,3-dideoxy-β-D-ribofuranosyl)-7-methyl-3H-pyrano[2,3-d]pyrimidine-2,5-dione
  参考文献：
  名称：

  导致双环嘧啶核苷和苯并吡喃-4-酮的串联反应。

  摘要：

  已经开发了通过高炔丙醇的氧化和随后的异构化，将烯醇分子内加成到烯丙基酮中的新颖，快速，有效的双环嘧啶核苷和苯并吡喃-4-酮的合成方法。这种方法为结构和药学上有趣的吡喃并[2,3 - d ]嘧啶-2,5-二酮核苷和苯并吡喃-4-酮衍生物提供了有效而有前途的方法。

  DOI：

  10.1021/jo102131y

文献信息

• An Efficient Synthesis of 2-Substituted Benzoxazoles via RuCl3·3H2O Catalyzed Tandem Reactions in Ionic Liquid
  作者：Xuesen Fan、Yan He、Yangyang Wang、Xinying Zhang、Jianji Wang

  DOI：10.1002/cjoc.201190156

  日期：2011.4

  An efficient synthesis of 2‐substituted benzoxazoles through RuCl3·3H2O catalyzed, air oxidized tandem reactions of 2‐aminophenols and aldehydes in [bmim]BF4 was developed. This synthetic strategy has such advantages as mild reaction conditions, cost‐free oxidant, readily available starting materials, and recyclable catalyst and solvent. As an application, it was successfully used in the synthesis of

  通过RuCl 3 ·3H 2 O催化2-氨基苯酚和醛在[bmim] BF 4中的空气氧化串联反应，可以有效合成2-取代的苯并恶唑。这种合成策略具有以下优势：反应条件温和，氧化剂成本低，原料易得，可循环使用的催化剂和溶剂。作为一种应用，它已成功用于未报告的具有潜在生物活性的5-（苯并恶唑-2-基）-2 -′-脱氧尿苷的合成。
• Synthesis of 5-isoxazol-3-yl-pyrimidine nucleosides as potential antileishmanial agents
  作者：Shenghai Guo、Jiliang Wang、Xinying Zhang、Sandrine Cojean、Philippe M. Loiseau、Xuesen Fan

  DOI：10.1016/j.bmcl.2015.04.097

  日期：2015.7

  A simple and practical procedure for the preparation of C5-(isoxazol-3-yl)-pyrimidine nucleosides through 1,3-dipolar cycloaddition of the in situ formed C5-nitrile oxide substituted pyrimidine nucleosides with various terminal alkynes is presented. Compared with literature procedures, this new method has advantageous features such as readily available and inexpensive starting materials, simple procedure without using expensive transition metal catalyst, and broad scope of substrates. By employing this method, 30 nucleoside analogues were prepared in moderate yields. Biological studies on these C5-(isoxazol-3-yl)-pyrimidine nucleosides showed that most of them exhibited significant in vitro antileishmanial activity. (C) 2015 Elsevier Ltd. All rights reserved.