(2S,3S,4S,5R,6S)-2-(iodomethyl)-6-phenoxy-tetrahydropyran-3,4,5-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-2-(iodomethyl)-6-phenoxy-tetrahydropyran-3,4,5-triol
• 英文别名: (2S,3S,4S,5R,6S)-2-(iodomethyl)-6-phenoxyoxane-3,4,5-triol
• 化学式: C₁₂H₁₅IO₅
• 分子量: 366.15
• InChiKey: DZOVVAQRYWJSJE-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-2-(iodomethyl)-6-phenoxy-tetrahydropyran-3,4,5-triol 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 27.0h， 生成 1-(phenyl-2,3,4-O-acetyl-β-D-glucopyranosid-6-yl)-3-methylimidazolium iodide
  参考文献：
  名称：

  Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

  摘要：

  The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

  DOI：

  10.1002/ejoc.202400177

文献信息

• Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction
  作者：Hannes Ziems、Mirai Komabayashi、Paul Lehmann、Alexander Villinger、Stefan Jopp

  DOI：10.1002/ejoc.202400177

  日期：——

  The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.