(4aS*,6S*,8aR*)-1-benzyloxycarbonyl-6-propyl-5-(toluene-4-sulfonyl)octahydro-3-oxa-2-thia-1,5-diazanaphthalene 2,2-dioxide

• 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: (4aS*,6S*,8aR*)-1-benzyloxycarbonyl-6-propyl-5-(toluene-4-sulfonyl)octahydro-3-oxa-2-thia-1,5-diazanaphthalene 2,2-dioxide
• 英文别名: benzyl (4aS,6S,8aR)-5-(4-methylphenyl)sulfonyl-2,2-dioxo-6-propyl-4,4a,6,7,8,8a-hexahydropyrido[3,2-d]oxathiazine-1-carboxylate
• 化学式: C₂₄H₃₀N₂O₇S₂
• 分子量: 522.643
• InChiKey: BUEVYRBYDODDGB-MDNUFGMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4aS*,6S*,8aR*)-1-benzyloxycarbonyl-6-propyl-5-(toluene-4-sulfonyl)octahydro-3-oxa-2-thia-1,5-diazanaphthalene 2,2-dioxide 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以87%的产率得到(2S*,3R*,6S*)-2-azidomethyl-3-benzyloxycarbonylamino-6-propyl-1-(toluene-4-sulfonyl)piperidine
  参考文献：
  名称：

  Iterative Multifunctionalization of Unactivated C−H Bonds in Piperidines by Way of Intramolecular Rh(II)-Catalyzed Aminations

  摘要：

  Efficient stereocontrolled synthesis of di-, tri-, tetra-, and pentasubstituted piperidines from simple 2-sulfamoyloxymethyl piperidine derivatives has been performed by way of intramolecular Rh-catalyzed amination of saturated C-H bonds. In this process, the sulfamoyloxymethyl arm was directly or indirectly involved in the functionalization of every saturated methylene group of the piperidine ring at C-3, C-4, C-5, and C-6. Direct application to the total synthesis of iminosugars and related compounds demonstrated the synthetic potential of this strategy.

  DOI：

  10.1021/jo702350u
• 作为产物：
  描述：

  (4aS*,6S*,8aR*)-6-propyl-5-(toluene-4-sulfonyl)octahydro-3-oxa-2-thia-1,5-diazanaphthalene 2,2-dioxide 、 氯甲酸苄酯 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 为溶剂， 以72%的产率得到(4aS*,6S*,8aR*)-1-benzyloxycarbonyl-6-propyl-5-(toluene-4-sulfonyl)octahydro-3-oxa-2-thia-1,5-diazanaphthalene 2,2-dioxide
  参考文献：
  名称：

  Iterative Multifunctionalization of Unactivated C−H Bonds in Piperidines by Way of Intramolecular Rh(II)-Catalyzed Aminations

  摘要：

  Efficient stereocontrolled synthesis of di-, tri-, tetra-, and pentasubstituted piperidines from simple 2-sulfamoyloxymethyl piperidine derivatives has been performed by way of intramolecular Rh-catalyzed amination of saturated C-H bonds. In this process, the sulfamoyloxymethyl arm was directly or indirectly involved in the functionalization of every saturated methylene group of the piperidine ring at C-3, C-4, C-5, and C-6. Direct application to the total synthesis of iminosugars and related compounds demonstrated the synthetic potential of this strategy.

  DOI：

  10.1021/jo702350u