(1R,4R,5S)-2-Benzyl-4-hydroxy-7-dimethyl-6,8-dioxa-2-azabicyclo<3.4.0>nonane | 163060-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,4R,5S)-2-Benzyl-4-hydroxy-7-dimethyl-6,8-dioxa-2-azabicyclo<3.4.0>nonane
• CAS: 163060-77-3
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: YJUPYLVLYMCNJD-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.38
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S)-2-Benzyl-4-hydroxy-7-dimethyl-6,8-dioxa-2-azabicyclo<3.4.0>nonane 在 溶剂黄146 作用下， 反应 0.5h， 生成 (2R,3S,4R)-2-(Hydroxymethyl)-3,4-dihydroxy-1-benzylpyrrolidine
  参考文献：
  名称：

  A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations

  摘要：

  A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.

  DOI：

  10.1021/jo00106a021
• 作为产物：
  描述：

  (1R,5S)-2-Benzyl-7,7-dimethyl-6,8-dioxa-2-azabicyclo<3.4.0>nonan-4-one 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到(1R,4R,5S)-2-Benzyl-4-hydroxy-7-dimethyl-6,8-dioxa-2-azabicyclo<3.4.0>nonane
  参考文献：
  名称：

  A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations

  摘要：

  A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.

  DOI：

  10.1021/jo00106a021

文献信息

• A Practical and Divergent Way to Trihydroxylated Pyrrolidine Derivatives as Potential Glycosidase Inhibitors via Stereoselective Intermolecular cis-Amidoalkylations
  作者：Youngha Ryu、Guncheol Kim

  DOI：10.1021/jo00106a021

  日期：1995.1

  A practical and divergent way from the common tartrimide 1 to trihydroxylated pyrrolidines 2a-h as potential glycosidase inhibitors has been developed. cis-Amidoalkylations on the acyliminium intermediate 5 of the corresponding TBS-protected tartaric imide with the tin reagents afforded the desired structures 6a-c in good yields and high selectivities. In this reaction the adjacent OTBS group controls the stereoselectivity in the presence of a Lewis acid MgBr2. Transformations to each desired pyrrolidine could be achieved via efficient methods including selective protection, functionalization of the unsaturated bonds, and reduction of the amide group.