N,N'-bis(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea | 1241901-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N,N'-bis(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea
• 英文别名: (1S,2R,6R,7S,9R,12R)-5-[(1S,2R,6R,7S,9R,12R)-4-oxo-12-phenyl-7-prop-2-enoxy-3,8,11,13-tetraoxa-5-azatricyclo[7.4.0.02,6]tridecane-5-carbonyl]-12-phenyl-7-prop-2-enoxy-3,8,11,13-tetraoxa-5-azatricyclo[7.4.0.02,6]tridecan-4-one
• CAS: 1241901-05-2
• 化学式: C₃₅H₃₆N₂O₁₃
• 分子量: 692.676
• InChiKey: ILBKUEOSIOINFY-VKVZWYSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  50
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  N,N'-bis(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea 在 水 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以76%的产率得到N,N'-bis(1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranos-2-yl)urea
  参考文献：
  名称：

  尿素连接的氨基葡萄糖二聚体作为合成线性和环状新糖的基础

  摘要：

  通过对 2,3-氨基醇单体的标准恶唑烷酮闭合反应的修改，获得了一种新型的脲连接葡糖胺二聚体，并通过 NMR 光谱和分子力学和动力学技术进行了充分表征。提出了一种基于形成 2,3-双[(对硝基苯氧基)羰基] 中间体的二聚反应机制。对二聚体正交保护基团模式的化学选择性操作——尤其是在其前所未有的恶唑烷酮-脲-恶唑烷酮系统上——提供了一种醇结构单元，可用于获得更高的线性和环状新糖。新型氨基甲酸酯连接的新二糖大环的构象特征和 3D 表征是通过分子力学和动力学计算完成的。

  DOI：

  10.1002/ejoc.201000292
• 作为产物：
  描述：

  allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 sodium hydride 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 1.25h， 生成 N,N'-bis(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea
  参考文献：
  名称：

  Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

  摘要：

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.005

文献信息

• A Urea-Linked Glucosamine Dimer as a Building Block for the Synthesis of Linear and Cyclic Neosaccharides
  作者：Luigi Cirillo、Alba Silipo、Emiliano Bedini、Michelangelo Parrilli

  DOI：10.1002/ejoc.201000292

  日期：2010.7

  A novel urea-linked glucosamine dimer was obtained through a modification of the standard oxazolidinone closure reaction on a 2,3-amino alcohol monomer and fully characterized by NMR spectroscopy and by molecular mechanics and dynamics techniques. A mechanism was proposed for the dimerization reaction that was based on the formation of a 2,3-bis[(p-nitrophenoxy)carbonyl] intermediate. Chemoselective

  通过对 2,3-氨基醇单体的标准恶唑烷酮闭合反应的修改，获得了一种新型的脲连接葡糖胺二聚体，并通过 NMR 光谱和分子力学和动力学技术进行了充分表征。提出了一种基于形成 2,3-双[(对硝基苯氧基)羰基] 中间体的二聚反应机制。对二聚体正交保护基团模式的化学选择性操作——尤其是在其前所未有的恶唑烷酮-脲-恶唑烷酮系统上——提供了一种醇结构单元，可用于获得更高的线性和环状新糖。新型氨基甲酸酯连接的新二糖大环的构象特征和 3D 表征是通过分子力学和动力学计算完成的。
• Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols
  作者：Emiliano Bedini、Luigi Cirillo、Michelangelo Parrilli

  DOI：10.1016/j.tet.2012.12.005

  日期：2013.1

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.