(2R,3R,4R,Z)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(4-methoxybenzylidene)-4-(piperidin-1-yl)tetrahydrofuran-3-ol | 1174427-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R,4R,Z)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(4-methoxybenzylidene)-4-(piperidin-1-yl)tetrahydrofuran-3-ol
• 英文别名: (2S,3R,4R,5Z)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4-methoxyphenyl)methylidene]-4-piperidin-1-yloxolan-3-ol
• CAS: 1174427-51-0
• 化学式: C₂₂H₃₁NO₅
• 分子量: 389.492
• InChiKey: MIESZHQHHNMKHT-OTLGCGHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3R,4R,Z)-5-(bromomethylene)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-(piperidin-1-yl)tetrahydrofuran-3-ol 、 4-甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以73%的产率得到(2R,3R,4R,Z)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(4-methoxybenzylidene)-4-(piperidin-1-yl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Three-Component Assembly of Amines, Boronic Acids, and a Polyfunctionalized Furanose: A Concise Entry to Furanose-Based Carbohydrate Templates

  摘要：

  A highly functionalyzed furanose derivative, accessible in five steps from D-mannose, comprising a halo-alkenyl allylic-oxirane system, undergoes a palladium catalyzed one-pot, three component, assembly with boronic acids (or alkyl boranes) and amines to give, in a complete regio- and stereocontrolled Manner, a sugar based derivative with two sites of molecular diversity.

  DOI：

  10.1021/jo9012817

文献信息

• Three-Component Assembly of Amines, Boronic Acids, and a Polyfunctionalized Furanose: A Concise Entry to Furanose-Based Carbohydrate Templates
  作者：Ana M. Gómez、Aitor Barrio、Ana Pedregosa、Serafín Valverde、J. Cristóbal López

  DOI：10.1021/jo9012817

  日期：2009.8.21

  A highly functionalyzed furanose derivative, accessible in five steps from D-mannose, comprising a halo-alkenyl allylic-oxirane system, undergoes a palladium catalyzed one-pot, three component, assembly with boronic acids (or alkyl boranes) and amines to give, in a complete regio- and stereocontrolled Manner, a sugar based derivative with two sites of molecular diversity.