1-[(2R,3R,4R,5R)-5-(azidomethyl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]pyrimidine-2,4-dione | 669012-97-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-[(2R,3R,4R,5R)-5-(azidomethyl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 669012-97-9
• 化学式: C₂₁H₃₉N₅O₅Si₂
• 分子量: 497.742
• InChiKey: GEHVJKLSGOZOMZ-VBSBHUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  131.31
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4R,5R)-5-(azidomethyl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]pyrimidine-2,4-dione 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylcarbamoyloxy]ethyl N-[[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methyl]carbamate
  参考文献：
  名称：

  The First Direct Evaluation of the Two-Active Site Mechanism for Chitin Synthase

  摘要：

  Chitin synthase polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-G1cNAc) and is essential for fungal cell wall biosynthesis. The alternating orientation of the GlcNAc residues within the chitin chain has led to the proposal that chitin synthase possesses two active sites. We report the results of the first direct test of this possibility. Two simple uridine-derived dimeric inhibitors are shown to exhibit 10-fold greater inhibition than a monomeric control, consistent with the presence of two active sites. This observation has important implications for the development of antifungal agents, as well as the understanding of polymerizing glycosyltransferases.

  DOI：

  10.1021/jo035100c
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 4-二甲氨基吡啶 、 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 1-[(2R,3R,4R,5R)-5-(azidomethyl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  The First Direct Evaluation of the Two-Active Site Mechanism for Chitin Synthase

  摘要：

  Chitin synthase polymerizes UDP-GlcNAc to form chitin (poly-beta(1,4)-G1cNAc) and is essential for fungal cell wall biosynthesis. The alternating orientation of the GlcNAc residues within the chitin chain has led to the proposal that chitin synthase possesses two active sites. We report the results of the first direct test of this possibility. Two simple uridine-derived dimeric inhibitors are shown to exhibit 10-fold greater inhibition than a monomeric control, consistent with the presence of two active sites. This observation has important implications for the development of antifungal agents, as well as the understanding of polymerizing glycosyltransferases.

  DOI：

  10.1021/jo035100c

文献信息

• Rh(I)-Catalyzed Coupling of Azides with Boronic Acids Under Neutral Conditions
  作者：Shiyang Xu、Hong Guo、Yuhan Liu、Wenxu Chang、Jiyao Feng、Xiongkui He、Zhenhua Zhang

  DOI：10.1021/acs.orglett.2c02053

  日期：2022.8.5

  importance of polyfunctional amines, C–N bond formation is important in synthetic organic chemistry. Here we present a neutral amination reaction using azides as the nitrogen source and arylboronic acids with a rhodium(I) catalyst to afford alkyl–aryl and aryl–aryl secondary amines. Natural products and pharmaceutical derivatives were applied, and gram-scale reactions were performed, which demonstrated the

  由于多官能胺的重要性，C-N 键的形成在合成有机化学中很重要。在这里，我们提出了使用叠氮化物作为氮源和芳基硼酸与铑 (I) 催化剂的中性胺化反应，得到烷基-芳基和芳基-芳基仲胺。应用了天然产物和药物衍生物，并进行了克级反应，证明了其效用。机械实验和 DFT 计算表明该反应涉及金属-氮烯中间体。