1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-iodouracil | 1372610-31-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-iodouracil
• 英文别名: 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-iodorouracil；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-iodo-2,4-dioxopyrimidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 1372610-31-5
• 化学式: C₁₈H₂₁IN₂O₁₁
• 分子量: 568.276
• InChiKey: UDGXUCXYLABAHY-OWVAZHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-iodouracil 在 copper(l) iodide 、 四(三苯基膦)钯 、 氨 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.05h， 生成 1-(β-D-glucopyranosyl)-5-[(p-pentylphenyl)ethynyl]uracil
  参考文献：
  名称：

  Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

  摘要：

  A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.092
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 、 5-碘尿嘧啶 在 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 、 糖精 作用下， 以 乙腈 为溶剂， 反应 0.05h， 以83%的产率得到1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-iodouracil
  参考文献：
  名称：

  Rapid microwave-enhanced synthesis of C5-alkynyl pyranonucleosides as novel cytotoxic antitumor agents

  摘要：

  A microwave-assisted, one-pot, coupling reaction for the synthesis of C5-alkynyl-uracil and cytosine glucopyranonucleosides has been developed. The reaction is carried out under standard Sonogashira coupling conditions from glucopyranonucleosides of 5-iodouracil or 5-iodocytosine and various terminal alkynes. All compounds were evaluated for their cytostatic and antiviral activity. The 5-phenylethynyluracil pyranonucleoside derivative 6a showed the most promising cytostatic activity (50% inhibitory concentration in the lower micromolar range). No meaningful antiviral activity was recorded. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.092

文献信息

• A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N -glycosylation
  作者：Nabamita Basu、Kin-ichi Oyama、Masaki Tsukamoto

  DOI：10.1016/j.tetlet.2017.03.046

  日期：2017.5

  A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer

  研究了固体负载的酸性高氯酸恶唑鎓盐在N-糖基化反应中的非均相催化剂，该反应使用甲硅烷基化的修饰的嘧啶和酰化的核糖或葡萄糖得到相应的嘧啶核苷。该盐是非吸湿性和稳定粉末，其活性与高氯酸2-甲基-5-苯基苯并恶唑鎓的活性相当。与该聚合物催化剂的反应可以以克为单位进行。还研究了固体负载催化剂的可重复使用性。
• 一种三价碘试剂参与的糖苷化方法
  申请人：华中科技大学

  公开号：CN116554245A

  公开（公告）日：2023-08-08

  一种三价碘试剂参与的糖苷化方法，其特征在于，糖基供体(I)在三价碘试剂、过渡金属催化剂存在下活化，然后与受体(II)在酸催化下反应或直接反应，得到糖苷化产物(III)；所述糖基供体(I)中，Gly为糖环上一个或多个羟基被保护基保护的糖基；X为氧、硫或硒原子；R为烷基或芳基；所述受体(II)选自含有一个或多个自由羟基的糖类、醇类、酚类、黄酮类、羧酸类、磷酸类、嘧啶类、嘌呤类、酰胺类、磺酰胺类、胍类、芳基胺类、吲哚类、烯醇硅醚类、硫醇或硫酚类亲核试剂。
• Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate
  作者：Hiroshi Shirouzu、Hiroki Morita、Masaki Tsukamoto

  DOI：10.1016/j.tet.2014.03.013

  日期：2014.6

  Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5-phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales. (C) 2014 Elsevier Ltd. All rights reserved.