2-(piperidin-1-yl)ethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose | 316352-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(piperidin-1-yl)ethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-6-(hydroxymethyl)-5-phenylmethoxy-2-(2-piperidin-1-ylethoxy)-4-(propan-2-ylcarbamoyloxy)oxan-3-yl] benzoate
• CAS: 316352-91-7
• 化学式: C₃₁H₄₂N₂O₈
• 分子量: 570.683
• InChiKey: NGYJPMCJNYGEPG-OVFYEYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(piperidin-1-yl)ethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以86%的产率得到2-(piperidin-1-yl)ethyl 4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-d-Glucose Scaffold

  摘要：

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.

  DOI：

  10.1021/jo001099v
• 作为产物：
  描述：

  thioethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2-(piperidin-1-yl)ethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-d-Glucose Scaffold

  摘要：

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.

  DOI：

  10.1021/jo001099v

文献信息

• Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-<scp>d</scp>-Glucose Scaffold
  作者：Ralph Hirschmann、Laurent Ducry、Amos B. Smith

  DOI：10.1021/jo001099v

  日期：2000.12.1

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.