26,28-bis({(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-hexahydropyrrolo[1,2-b]isoxazol-2-yl}methoxy)-25,27-dihydroxy-calix[4]arene | 1386987-69-4

• 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: 26,28-bis({(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-hexahydropyrrolo[1,2-b]isoxazol-2-yl}methoxy)-25,27-dihydroxy-calix[4]arene
• 英文别名: 26,28-bis[[(2R,3aR,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b][1,2]oxazol-2-yl]methoxy]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol
• CAS: 1386987-69-4
• 化学式: C₈₆H₈₆N₂O₁₂
• 分子量: 1339.64
• InChiKey: UJXKVQXHPBZGMM-UKWGUYAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  100
• 可旋转键数：
  26
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  26,28-bis({(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-hexahydropyrrolo[1,2-b]isoxazol-2-yl}methoxy)-25,27-dihydroxy-calix[4]arene 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 1.5h， 以66%的产率得到26,28-bis[(2R)-3-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)pyrrolidin-2-yl]-2-hydroxypropoxy]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-25,27-diol
  参考文献：
  名称：

  Building Multivalent Iminosugar-Based Ligands on Calixarene Cores via Nitrone Cycloadditions

  摘要：

  A novel and challenging approach for the construction of multivalent iminosugar architectures directly on calixarene scaffolds is presented, which exploits multiple cycloaddition reactions of a carbohydrate-derived nitrone on diversely functionalized calix[4]arenes. Regardless of the 4-fold reiteration on a single calixarene, the reactions take place with high regio- and stereoselectivity, demonstrating this method as an appealing one for the synthesis of calixarene-based neoglycoconjugates.

  DOI：

  10.1021/jo301155p
• 作为产物：
  描述：

  25,27-dihydroxy-26,28-bis(prop-2-en-1-yloxy)calix[4]arene 、 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 以 甲苯 为溶剂， 反应 72.0h， 以52%的产率得到26,28-bis({(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-hexahydropyrrolo[1,2-b]isoxazol-2-yl}methoxy)-25,27-dihydroxy-calix[4]arene
  参考文献：
  名称：

  Building Multivalent Iminosugar-Based Ligands on Calixarene Cores via Nitrone Cycloadditions

  摘要：

  A novel and challenging approach for the construction of multivalent iminosugar architectures directly on calixarene scaffolds is presented, which exploits multiple cycloaddition reactions of a carbohydrate-derived nitrone on diversely functionalized calix[4]arenes. Regardless of the 4-fold reiteration on a single calixarene, the reactions take place with high regio- and stereoselectivity, demonstrating this method as an appealing one for the synthesis of calixarene-based neoglycoconjugates.

  DOI：

  10.1021/jo301155p

文献信息

• Building Multivalent Iminosugar-Based Ligands on Calixarene Cores via Nitrone Cycloadditions
  作者：Francesca Cardona、Giovanni Isoldi、Francesco Sansone、Alessandro Casnati、Andrea Goti

  DOI：10.1021/jo301155p

  日期：2012.8.17

  A novel and challenging approach for the construction of multivalent iminosugar architectures directly on calixarene scaffolds is presented, which exploits multiple cycloaddition reactions of a carbohydrate-derived nitrone on diversely functionalized calix[4]arenes. Regardless of the 4-fold reiteration on a single calixarene, the reactions take place with high regio- and stereoselectivity, demonstrating this method as an appealing one for the synthesis of calixarene-based neoglycoconjugates.