2,4-Bis(trimethylsilyl)-5-methoxyuracil | 37805-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-Bis(trimethylsilyl)-5-methoxyuracil
• 英文别名: 5-methoxy-2,4-bis-trimethylsilanyloxy-pyrimidine；(5-Methoxy-2-trimethylsilyloxypyrimidin-4-yl)oxy-trimethylsilane
• CAS: 37805-85-9
• 化学式: C₁₁H₂₂N₂O₃Si₂
• 分子量: 286.478
• InChiKey: AMMCKIDNGXVKOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  306.9±52.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 2,4-Bis(trimethylsilyl)-5-methoxyuracil 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 4.0h， 以89%的产率得到5-甲氧基尿苷 2',3',5'-三苯甲酸酯
  参考文献：
  名称：

  Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255

  摘要：

  DOI：
• 作为产物：
  描述：

  六甲基二硅氮烷 、 5-甲氧基-2,4-二羟基嘧啶 在 ammonium sulfate 作用下， 生成 2,4-Bis(trimethylsilyl)-5-methoxyuracil
  参考文献：
  名称：

  Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists

  摘要：

  P2Y(6) receptor (P2Y(6)-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y(6)-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5'-alpha,beta-methylene-diphosphonate, 16 and 23, or lack of 2'-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y(6)-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y(6)-R (IC50 112 mu M) versus P2Y(2)/(4)-Rs. In summary, we have established a comprehensive SAR for hP2Y(6)-R ligands towards the development of hP2Y(6)-R antagonists. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.004

文献信息

• The first intermolecular interrupted imino-Nazarov reaction: expeditious access to carbocyclic nucleoside analogues
  作者：Ronny William、Wei Lin Leng、Siming Wang、Xue-Wei Liu

  DOI：10.1039/c5sc03559g

  日期：——

  Nazarov reaction suffers from unfavorable energetics associated with the ring closure process, thereby limiting the utility of this class of reactions. In this report, the realization of the first intermolecular interrupted imino-Nazarov reaction utilizing silylated pyrimidine derivatives as nucleophilic trapping partners culminated in an expedient synthetic route to carbocyclic nucleoside analogues. The

  纳扎罗夫反应的类似亚氨基变体具有与闭环过程相关的不利的能量，从而限制了这类反应的效用。在本报告中，利用甲硅烷基化的嘧啶衍生物作为亲核捕获伙伴实现了第一个分子间亚氨基-Nazarov间断反应，最终实现了合成碳环核苷类似物的简便途径。在Nazarov反应的其他变体中，甲硅烷基化的核碱基在拦截羟基烯丙基阳离子方面的潜在应用为开发形成碳环核苷类似物的新策略提供了巨大的机会。
• Vorbrueggen, Helmut; Krolikiewicz, Konrad; Bennua, Baerbel, Chemische Berichte, 1981, vol. 114, # 4, p. 1234 - 1255
  作者：Vorbrueggen, Helmut、Krolikiewicz, Konrad、Bennua, Baerbel

  DOI：——

  日期：——
• Vorbrueggen, Helmut; Hoefle, Gerhard, Chemische Berichte, 1981, vol. 114, # 4, p. 1256 - 1268
  作者：Vorbrueggen, Helmut、Hoefle, Gerhard

  DOI：——

  日期：——
• Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists
  作者：Diana Meltzer、Ophir Ethan、Guillaume Arguin、Yael Nadel、Ortal Danino、Joanna Lecka、Jean Sévigny、Fernand-Pierre Gendron、Bilha Fischer

  DOI：10.1016/j.bmc.2015.07.004

  日期：2015.9

  P2Y(6) receptor (P2Y(6)-R) is involved in various physiological and pathophysiological events. With a view to set rules for the design of UDP-based reversible P2Y(6)-R antagonists as potential drugs, we established structure-activity relationship of UDP analogues, bearing modifications at the uracil ring, ribose moiety, and the phosphate chain. For instance, C5-phenyl- or 3-NMe-uridine-5'-alpha,beta-methylene-diphosphonate, 16 and 23, or lack of 2'-OH, in 12-15, resulted in loss of both agonist and antagonist activity toward hP2Y(6)-R. However, uridylyl phosphosulfate, 19, selectively inhibited hP2Y(6)-R (IC50 112 mu M) versus P2Y(2)/(4)-Rs. In summary, we have established a comprehensive SAR for hP2Y(6)-R ligands towards the development of hP2Y(6)-R antagonists. (C) 2015 Elsevier Ltd. All rights reserved.