(2R,3S,4R,5R)-N-allyl-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-amine | 1041433-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R)-N-allyl-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-amine
• 英文别名: (2R,3S,4R,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)-N-prop-2-enyloxolan-3-amine
• CAS: 1041433-36-6
• 化学式: C₂₃H₂₉NO₄
• 分子量: 383.488
• InChiKey: LMEUBFYQRLFYHL-WZYRSQIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-N-allyl-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-amine 在 trityl tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (2R,3S,4R,5R)-3-(allylamino)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2-ol 、 (2S,3S,4R,5R)-3-(allylamino)-4-(benzyloxy)-5-(benzyloxymethyl)tetrahydrofuran-2-ol
  参考文献：
  名称：

  Mild and Efficient Chemoselective Deprotection of Anomeric O-Methyl Glycosides with Trityl Tetrafluoroborate

  摘要：

  A facile chemoselective deprotection of anomeric O-methyl glycosides has been achieved in good to excellent yields within 10-40 min with use of trityl tetrafluoroborate in dichloromethane at ambient temperatures. The present method is easily implemented and tolerates different functional groups.

  DOI：

  10.1021/jo800693w
• 作为产物：
  描述：

  (2R,3S,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-amine 、 3-溴丙烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到(2R,3S,4R,5R)-N-allyl-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-amine
  参考文献：
  名称：

  Mild and Efficient Chemoselective Deprotection of Anomeric O-Methyl Glycosides with Trityl Tetrafluoroborate

  摘要：

  A facile chemoselective deprotection of anomeric O-methyl glycosides has been achieved in good to excellent yields within 10-40 min with use of trityl tetrafluoroborate in dichloromethane at ambient temperatures. The present method is easily implemented and tolerates different functional groups.

  DOI：

  10.1021/jo800693w

文献信息

• Mild and Efficient Chemoselective Deprotection of Anomeric <i>O</i>-Methyl Glycosides with Trityl Tetrafluoroborate
  作者：Amit Kumar、Venkata Ramana Doddi、Yashwant D. Vankar

  DOI：10.1021/jo800693w

  日期：2008.8.1

  A facile chemoselective deprotection of anomeric O-methyl glycosides has been achieved in good to excellent yields within 10-40 min with use of trityl tetrafluoroborate in dichloromethane at ambient temperatures. The present method is easily implemented and tolerates different functional groups.